J buckingham, r a hill (auth ) atlas of stereochemistry absolute configurations of organic molecules springer US (1986)

ATLAS OF STEREOCHEMISTRY Absolute Configurations o/Organic Moleeules... British Library Cataloguing in Publication Data Klyne, William Atlas of stereochemistry: absolute configurations

Atlas of

Stereochemistry

SUPPLEMENT

ATLAS OF STEREOCHEMISTRY

Absolute Configurations o/Organic Moleeules

ISBN 978-0-412-26000-1 ISBN 978-1-4899-3420-8 (eBook)

DOI 10.1007/978-1-4899-3420-8

© 1986 J Buckingham and R.A Hili

Originally published by Chapman and Hall in 1986

Softcover reprint ofthe hardcover 2nd edition 1986

All rights reserved No part of this book may be reprinted,

or reproduced or utilized in any form or by any electronic, mechanical or other means, now known or hereafter invented, inc1uding photocopying and recording, or in any information storage and retrieval system, without

permission in writing from the publisher

British Library Cataloguing in Publication Data

Klyne, William

Atlas of stereochemistry: absolute configurations of

organie molecules.-2nd ed supplement

Atlas of stereochemistry, absolute configurations of

organic molecules, second edition Supplement

Supplement to: Atlas of stereochemistry: absolute

configurations of organie molecularesIW Klyne and J

Buckingham 2nd ed London, 1978

Bibliography: p

Inc1udes indexes

1951-11 Klyne, William Atlas of stereochemistry

111 Title

00481.K64 1978 Suppl 541.2'23 85-12825

Contents

X" Compounds exhibiting Axial or Plan ar Chirality;

Preface to the Supplement

Tbe determination of absolute configurations is now a central and routine part of research in organic chemistry and biochemistry Since the publication of the second edition of the Atlas in

1978, many hundred further important determinations have been carried out, more than justifying the present publication of an extensive supplement

Despite some expectations to the contrary, direct Bijvoet X-ray determinations have not completely dominated the field in the last seven years Chemical correlations continue to be the method of choice for most types of compound except complex natural products; the correlation charts which are the raison d' etre of this publication continue to prosper , as perusal of the pages

of this supplement will show

Once again, our thanks to those reviewers and correspondents who have sent in their comments on published correlations Tbere have been relatively few absolute configuration reversals during the last seven years, leading to the presumption that the vast majority of the determinations so far recorded in the Atlas will stand the test of time

J Buckingham R.A Hill

Key to the Supplement

Numbering of formulae and cross-references

The arrangement of chapters is the same as in the Main Work In the supplement each compound reference carries a second prime Thus A32.2 refers to volume 1 of the Main Work, A'32.2 to volume 2, and A"32.2 to the Supplement

Important generalliterature references

Proposals modifying the Cahn-Ingold-Prelog system of configurational notation have been put

forward by V Prelog and G Heimchen (Angew Chem., Int Ed Eng/., 1982, 21, 567)

1977 saw the publication of the major work Stereochemistry Fundamentals and Methods, Georg

Thieme Verlag In particular volume 3 is entitled 'Determination of ~onfigurations by Chemical Methods' and volume 4, by J Jaques, C Cross and S Bourcier gives the absolute configurations

of 6000 selected compounds with one chiral carbon atom in tabular form

For a discussion of the Bijvoet X-ray anomalous dispersion method, see D Rogers, Acta

The publication of the series Atlas of Three-dimensional structure of drugs (Janssen Research

Foundation Series) began in 1979 with Vol 1 edited by J.P Tolleaere,'H Moereels and L.A Raymaekers, published by Elsevier, Amsterdam

The theory of 'hyperchirality' advanced by J Dugundy, D Marquarding and I Ugi (Chem Ser 1976,9, 74; 1977, 11, 17), seems to have passed into the limbo of history (W Hasselbarth, ibid,

1976, 10, 96; 1977, 11, 148; C.A Mead, ibid, 1976, 10, 101; 1977, 11, 145)

Sub-c1assification of compounds in chapter A"

Class 1a

(SK-) I-omillo-2- proponephosphO"ic acid

methyl-Abs X"OY [I]

1 T Glowiak, W Sawka-Dobrowalska, J Kowalik, P Mastalerz, M Soroka and J Zon, Tetrahedron Lett., 1m, 3965

(211,311)-(+l2,3-Class 2a

CH]

B'+H C2H~

(I1H-) 2-brcmobulone A1.1I _._ _ _ _ _ _._._ _ _ _._.1._._._._._._ _ _ _ _ _ _._ _ - ' - ''''1

(5,sH+lcyclohoxyl-ether,

1 G Lowe and B.V.L Potter, J Chern Soc., Perkin Trans 1, 1980, 2029

2 S Fushiya, Y Sato and S Nozoe, Chern Lett 1980, 1215

3 B Seuring and D Seebach, Helv Chirn Acta, 1977, 60, 1175

4 N.K Chauduri, T.l Ball and N Finch, Experientia, 1977, 33, 575

5 D.L Boger and l.S Panek, J Org Chern., 1981, 46, 1208

CH,cHzOH

(SH ) 2-omlno- hyd,oxybulonoe ocie! A" 7

4-15 (5H-) (2-

b,omoethyll-oxirane Y" 10

i <S)-(-lpn>pylo.irono

A15.18

6 D.D Tanner, G.V Blackburn, Y Kosugi and T.C.S Rao, J Arn Chern Soc., 1977, 99, 2714

7 R.L Coumbie, D.D Ridley and G.W Simpson, Chern Cornrn., 1977, 315

8 R.C Hayward, C.H Overton and G.H Whitham, J Chern Soc., Perkin Trans 1, 1976, 2413

9 P.G Barili, G BeUucci, G Ingrosso and A Vatteroni, Gazz Chirn Ila1., 1977, 107, 147

Mo "'hor(-)'

EI ."ore-)

t [al j (4)

•

CH2COOH H+OH CCHz)6CH 3

S,S-di-MoC+)

1 K Mori, Tetrahedron, 1981, 37, 1341

8 CZS,3SI-f-)

1.4-d,tNone-2,!-dlCgrboxyhc aCid

2 H.R Schuler and K.N Slessor, Can J Chern., 1977, 55, 3280

3 M Segi, T Takebe, S Masuda, T Nakajima and S Suga, Bull Chern Soc Jpn., 1982, 55, 167

(lR,ZR)-(-) cyclohexone· , , 2 -

~C=CH

S (SH-loc\·l-yn-4-01

By AS(H) [.J]

+ (al 1 [JJ

+

H + ) : 3 C=CH

C(41 tC7]

CHzPl1 H+OH CH(CH 5 )z

14

(SH-)3-molhyl-4-phonylbulan- 2-01

Class 2a

2 B.R Davis, G.W Rewcastle, R.J Stevenson and P.D Woodgate, J Chern Soc., Perkin Trans 1, 1977, 2148

3 W.J McGahren, K.J Sax, M.P Kunstmann and G.A Ellestad, J Org Chern., 1977, 42, 1659

4 D.W Connell and M.D Sutherland, Aust J Chern., 1969, 22, 1033

5 P.A Levene and A Walti, J Biol Chern., 1931, 94, 593

6 D.R Crump, Aust J Chern., 1982, 35, 1945

7 J.P Vigneron, M Dhaenens and A Horeau, Tetrahedron, 1977, 33, 507

8 K Chan, N Cohen J.P DeNoble, A.C Specian and G Sauey, J Org Chern., 1976, 41, 3497

9 W.J Elliott and J Fried, J Org Chern., 1976, 41, 2469

J6-diow:o-6 (RH+)4-hydroxyhoxonoic 7 (R)-(+)4,-hycl roxynononoic I

5-dihydroxy-AI1 12

C(3Ij[4]

(5)-(+) IIlutamic acid A 11_7

C(~I![/]

oc;id loctcn •

(5 H+) t-arninoinclono

"ydrocrllotlde H A25.17

15 (5)-(+)3-ominop'opooo' 14 (SH )3-"""""'dipic 15

(S)-(+)2'amlno-2-l,I,3'1'icGtboxylic ocid _ (5-t.l,az~yl) butyrie acid_

(J -ca,boxYlilulomic) acid_ N-benzyloxycorbonyl,

18 5- ynoic acid 17 (5H )2,6-

(5)-(+)4-omlnohox-diam,nohox'l-yne_

hvd,ochlorldo (+)

<Io-Me sr.r (-)

The correlation All.15-+A18.2 is said to be dubious [6]

1 T.T Van, E Kojro and Z Grzonka, Tetrahedron , 1977, 33, 2299

2 P Casara, C Danzin, B.W Metcalf and M.J Jung, Chern Cornrn., 1982, 1190

3 J.L Morell, P Fleckenstein and E Gron, J Org Chern., 1977, 42, 355

4 See p All

5 U Ravid, R.M Silverstein and L.R Smith, Tetrahedron , 1978, 34, 1449

6 G Stork and A.F Kreft, J Arn Chern Soc., 1977, 99, 3851

7 L.R Smith, H.J Williams and R.M Silverstein, Tetrahedron Lett., 1978, 3231

8 E Balieu, P.M Boll and E Larsen, Acta Chern Scand., 1969, 23, 2191

9 C.T Clarke and J.H Jones, Tetrahedron Lett., 19n, 2367, and refs therein

10 J H Brewster, Helv Chim Acta, 1982, 65, 317, and refs therein; V Ghislandi and D Vercesi, Boll Chern., Farm., 1976, 115, 489

11 W Marki and R.S Schwyzer, Helv Chim Acta, 1976, 59, 1591

12 T Wieland, D Schermer, G Rohr and H Faulstich, Justus Liebigs Ann Chern., 1977, 806

13 Y Shimohigashi, M Waki and N lzumiya, Bull Chern Soc Jpn., 1979, 52, 949

(R)-(-)2-mol llyl- 3 ( - )nalo><lli" 4 (Sl-(-)ilomc.tachydme

/ mothylplpe,idino-2 -carboI<Ylic acid

«-(l-phonyl-propyl1mino) "'nzyl kt ton

: R = C2HO)' Abs X-roy ~/J

(RH )phenyl a-(l-phenylo' thyllmino) *zyl kotono

1 J.c Craig, S-Y.C Lee, W.E Pereira, H.C ßeyerman and L Maat, Tetrahedron, 1978, 34, 501

2 RH HilI and T Yuri, Tetrahedron, 1977, 33, 1569

3 O Cervinka, A Fabryova and V Novak, Collect Czech Chern Cornrnun, 1965, 30, 1742

4 I Kristensen, P.O Larsen and C.E Olsen, Tetrahedron, 1976, 32, 2799

5 F Kunz, J_ Retey, D Arigoni, L Tsai and T.C Stadtman, Helv Chim Acta, 1978, 61, 1139

6 A.V Robertson and L Marion, Can J Chern., 1959, 37, 829

7 K-H Michel, F Sandberg, F Haglid, T Norin, RP.K Chan and J.C Craig, Acta Chern Scand., 1969, 23, 3479

8 See p AIO

9 D Seebach and M Pohmakotr, He/v Chirn Acta., 1979, 62 843

10 A Wägner, Acta Crystallogr Sect B, 1980, 36, 77

11 I Fonseca, S Martinez-Carrera and S Garcia-ßlanco, Acta Crystallogr., Sect B, 1982, 38, 2735

12 R Parthasarathy, J.M Ohrt and G.ß Chheda, J Arn Chern Soc., 1974, 96, 8087

13 I Fonseca, S Martinez-Carrera ana S Garcia-ßlanco, Acta CrystalloJ(r., 1979, 35, 2643

-4 (RH+) I, 2 - qulnoline- 4 (3H)-one 11 (S)-(-) 2'onilina'

111

(S)-(+ ) I, 2 ' diomino' proponl A 18.'

1 M.P Paradisi and A Romeo, J Chern Soc., Perkin Trans 1, 1977, 596

2 P.S Portoghese, J Pharm Sei., 1964, 53, 228

3 A Fredga, Acta Chern Scand., Sero B, 1977, 31, 869

• Cut o [J']

10 (Rl-(-)2- bromo' propan-I- 01

13 (R H+13-bonzy lolY' 2·bromoprapon+oI

)4-mllhyl'2-4 W.L.F Armarego, B.A.Milloy and W Pendergast, J Chern Soc., Perkin Trans 1., 1976, 2229

5 See p A4

6 Y Yamamoto, J Oda and Y Inouye J Org Chern., 1976, 41, 303

7 L Maat and R.W Wulkan, Red Trav Chirn Pays-Bas, 1981, 100, 204

8 G Bettoni, C Franchini, R Perrone and V TortoreIla, Tetrahedron, 1980, 36, 409

9 B Ringdahl and R Dahlbom, Chern Scr., 1977, 12, 47

10 W.L.F Armarego, P Waring and J.W Williams, Chern Cornrnun., 1980, 334

11 W.L.F Armarego, H Schou and P Waring, J Chern Res (S), 1980, 133

12 S Matsuura and T Sugimoto, Bult Chern Soc Jpn., 1981, 54, 2543

13 T Sugimoto and S Matsuura, BulL Chern Soc Jpn., 1980, 53, 3385

14 D.D Miller, F Hsu, R.R Ruffolo and P.N Patil, J Med Chern., 1976, 19, 1382

15 A Lindquist, B Ringdahl, U Svensson and R Dahlbom, Acta Chern Scand., Sero B., 1976, 30, 517

(s H - )3-amino' I-pentyno A'II.9

CHa

CH:!COOH H2 N + H CH2CH:!CHa

CHa

(5H-)4-ominopenlaooc acid A' 14 14

N-phtholimide (-l

(5 )- (+)3-ominobulonoie acid A 19.9

1 W Oppolzer and G Flaskamp, Helv Chirn Acta, 1977, 60, 204

2 G Habermehl and H Andres, Justus Liebigs Ann Chern., 1977, 800

3 B Ringdahl and R Dahlbom, Acta Chern Scand., Sero B, 1976, 30, 812

4 B Ringdahl and R Dahlbom, Chern Scr., 1977, 12, 47

5 C.M Svahn and N.A Jonsson, Acta Chern Scand Sero B, 1978, 32, 137

6 G Lucente, G Piccinni and A Romeo, Gazz Chirn Ital., 1966, 96, 1380

8 R Kinas, K Pankiewicz, W.J Stec, P.B Farmer, A.B Foster and M Jarman, J Org Chern., 1977, 42, 1650

9 K.R Kopecky, P.M Pope and J.A Lopez Sastre, Can 1 Chern., 1976, 54, 2639

(5)-(- )2'om,no- (5)-(+12-hydroxy' 8 (5)(+ )3hydroxy

-pentonoie acid hexanoie acid 2-heptonone

8y AS (H) [1/] 12_ dihydroxyphonyl)- 5-hydro,y-(5)()l,7bi.(~,4

-3-hflptonone Ab' X-roy ~2J

i

1 S Yamada, T Mashiko and S Terashima, J Am Chern Soc., 1977, 99, 1988

2 P Dumas, N Spassky and P Sigwalt, Makromol Chern., 1972, 156, 55

3 J.L Coke and A.B Richon, J Org Chern., 1976, 41, 3516

4 M Masada and K Nishimura, Chern Lett., 1981, 1333

5 J.P Guette and N Spassky, Bull Soc Chirn Fr., 1972, 4217

6 G GottarelIi, B Samori, I Moretti and G Torre, J Chern Soc., Perkin Trans 2, 1977, 1105

7 R.E Ireland, C.S Wilcox and S Thaisrivongs, J Org Chern., 1978, 43, 786

8 A Konowal, J Jurczak and A Zamojski, Tetrahedron, 1976, 32, 2957

9 J Cleophax and S.D Gero, Bull_ Soc Chirn Fr., 1967, 1441

10 H Noguchi, U Sankawa and Y Iitaka, Acta Crystallogr., Sect B, 1978, 34, 3273

11 L Ananthasubramanian, S.T Carey and M.S.R Nair, Tetrahedron Lett., 1978, 3527

12 T Suga, S Ohta, T Hirata and T Aoki, Chern Lett., 1982, 895

Ht~)Ph

CH

I CH:z

111

14 mOlhyl )-2,5' dihyd<ofuroo

9.§OR ,91?)-(+)t~-methyl- 10

(SH+)3-oorboxymethyl-13 -ozotricyc lo [7.3 I 0 2• 7] 3,4-dihydrocorbo.ly,il 11 (S H+)!I-ominomol hyl-2-mel hyl- 3,4-di hyd,o- 12

13 _ OR,9S) : (+) I~- m"hy l- 2 7 i 14 (S)-(+)N-hydroxy- (S H+)omp/letomine A!!_ 10 I~ (S H+)2-I.ocyono

1~-QZOI"OYtlo[7 ,3 I 0 • ] i omphetomine Ab • X-roY[9J I - p/lonylpropone ,

-19 (2R,3R,4tJR,90RH-l

2-00.loxy- 3 -

t,lmethyl-ammoniodecalin iodid •

20 (R 5- hydroxylet,olin

H+)2-dipropylamino-Alls, X-",y ~61 Ab," X-roy ~71

Ab • X-roy ~~ I

1 T Hayashi, M Fukushima, M Konishi and M Kumada, Tetrahedron Leu., 1980, 79

2 e.e Tseng, S Terashima and S Yamada, Chern Pharrn Bull., 1977, 25, 29

3 R Buck, J Eberspächer and F Lingens, Justus Liebigs Ann Chern., 1979, 564

4 G.E Hein and C Niemann, J Am Chern Soc., 1962, 84, 4487

5 S.G Cohen and R.M Schultz, Proc Natl Acad Sei., USA, 1967, 57, 243

6 H Kato, E Koshinaka, T Nishikawa and Y Arata, Yakugaku Zasshi, 1974, 94, 934

7 T Wakabayashi and K Watanabe, Tetrahedron Leu., 1977, 4595

8 K Watanabe and T Wakabayashi, J Org Chern., 1980, 45, 357

9 H Herbert, Acta Crystallogr., Sect B, 1978, 34, 611

10 D.G Hay, F.J Leng, M.F Mackay and B Ternai, J Cryst Mol Struct., 1977, 7, 59

11 B Lindeke, G Anderson and U Paulsen Acta Chern Scand., Sero B, 1976, 30, 789

12 P Murray-Rust, J Murray-Rust, D Hartley and J Clifton, Acta Crystallogr., Sect B, 1982, 38, 306

13 M.P Periasamy and H.M Walborsky, J Am Chern Soc., 1977, 99, 2631

14 L.Y.Y Ma, N Camerman and A Camerman, Acta Crystallogr., Sect B, 1982, 38, 2861

15 K Yamada, M Takeda, N Itoh, N Umino, K Ikezawa, A Kiyomoto, K Aoe, K Kotera and T Iwakuma, Chern Pharrn Bull.,

1982, 30, 1588

16 B Lee and G.M Henry, Acta Crysta/logr., Sect B, 1976, 32, 938

17 J Giesecke, Acta Crystallogr., Sect B, 1980, 36, 110

I-phenyl-<t

AS ; [ ]

•

NHZ H,CCH 2 CH Z + H

11 (-) eiro modol

Abs X-roy (~

A 11"

1 T Glowiak , W Sawka-Dobrowolska, J Kowalik, P Mastalerz, M Soroka and J Zon, Tetrahedron Leu., 1977, 3965

2 K Lee, N Horowitz, J Ware and L.A Singer, J Arn Chern Soc., 1977, 99, 2622

3 O Cervinka, V Suchan, O Kotynek and V Dudek, Collect Czech Chern Cornrnun., 1965, 30, 2484

4 O Cervinka, V Dudek and V Senft, Collect Czech Chern Cornrnun., 1978, 43, 1087

5 N Furukawa, M Fukumura, T Nishio and S Oae, J Chern Soc., Perkin Trans 1, 1977,96

6 Y Masuda, Y Iitaka and H Hamano, Bull Chern Soc Jpn., 1974, 47, 825

7 F.R Ahmed and J Bagli, Can J Chern., 1982, 60, 2687

8 V Bertolasi, P.A Borea, G Gilli and M Sacerdoti, Acta Crystallogr Sect B, 1980, 36, 2287

9 W Stallings and J Donohue, J Cryst Mol Struct., 1981 , 11,59

2 R.K Hili and T.F Bradberry, Experientia, 1982, 38, 70

3 D Seebach, H Kalinowski, B Bastani, G Crass, H Daum, H Dörr, N.P Dupreez, V Ehrig, W Langer, C Nüssler, H Oei

and M Schmidt, Helv Chim Acta, 1977, 60, 301

4 M Imuta and H Ziffer, J Org Chem 1978, 43, 3319

5 K Mori, T Takigawa and M Matsui, Tetrahedron , 1979, 35, 833

6 M Imuta and H Ziffer, J Org Chem., 1978, 43, 3530

7 J.J Plattner and H Rapoport, J Am Chem Soc., 1971, 93, 1758

8 R.H Biom, J Am Chem Soc , 1945, 67, 494

9 M.D Fryzuk and B Bosnich, J Am Chem Soc., 1977, 99, 6262

10 M BucciareIli, A Fomi, I Moretti and G Torre, Tetrahedron, 1977, 33, 999

11 P.W Feit, Chem Ber., 1960, 93, 116

12 I.R.K Ness, H.G Fleteher and C.S Hudson, J Am Chern Soc., 1951 , 73, 4759

2-methy l- 3-phonyl- ! 8 ( 2R,35)(-)2 , 3' 9 ( 55,6R )(- ) 5 , 6- (lR,2S )(- ) 2-amino- 10 (45,5 R H -

)4,5-propionic acid ! dipheny l morphol'lne diphanylmorpholin r " 2-diph4!lnyl ethon~ d,phenyl - 2-oxozolldone

! CO : [ I) 3 - ono _CO : [I) A20.14 CO : [I)

Ph~_rO

°

11 ( 25,35)(-)2,3- 12 ( ~S ,6SH-)~,6- (l5,25)(- ) 2'o"'ino- HI (45,55

)-(-)4,5-111

diphenylmorpholine dipn.enylmorpholin- ' , 2 - dipn.enylethanol diphenyl - 2-oxozolidonf!l _

CD: [I) 3-0n0_ CD : [I) A 20.14 CD : [I)

)3-ornino-(25,35)(-)3' omino-2,3 a di pnenyl- p.-opon-I-ol A43 2

1!1 (45,55)(+)tolrohydro-4,5-diphe

nyl-2-Q)(ozolonll

1 W Klyne, P.M Scopes, N Berova, J Stefanovsky and B.J Kurtev, Tetrahedron, 1979, 35, 2009

2 G Fodor, J Stefanovsky and B.J Kurtev, Monatsh ehern., 1967, 98, 1027

3 X Schorno and E Steinegger, Experientia, 1979, 35, 572 •

4 J.N Stefanovsky, S.L Spassov, B.J Kurtev, M Balla and L ütvös, ehern Ber., 1969, 102, 717

5 G Fodor, J Stefanovsky and B.J Kurtev, ehern Ber., 1965, 98, 705

6 C.H Heathcock, C.T White, J.J Morrison and D van Derveer, J Org ehern., 1981, 46, 1296

)-(-)4-chlo,o-(Rl-{-) 4-mer blnzoin ( X = MI)

yl-(R)-(-) 1,2-diol A22 13

I - a l A' 18 14

CH=CH2 H+OH

Ph

13 §(5H-) I-phonyl' p<op-2-"' - 1-01

C(3)

-~I) (5 )-(-)2-hyd'oxy' 3- phonylp<oplonic acid

1 J Capillon and l-P Guette, Tetrahedron, 1979, 35, 1801

2 l.K Fraser, D.G Neilson, K.M Watson and J.W Heatlie, J Chem Soc., Perkin Trans 1, 1977,646

3 P.M Dansette, H Ziffer and D.M lerina, Tetrahedron, 1976, 32, 2071

4 I Iwai and K Tomita, J Pharm Soc Jpn., 1960, 80, 160

5 R Weidmann, A Schoofs and A Horeau, Bull Soc Chim Fr., 1976, 645

6 U Kuffner and K Schlogl, Monalsh Chem., 1972, 103, 1320

7 See p A22

8 W.H Pirkle, D.L Sikkenga and M.S Pavlin, J Org Chem , 1977, 42, 384

9 W.H Pirkle and l.R Hauske, J Org Chem., 1977, 42, 2436

10 M.H Delton and G.U Yuen, J Org Chem., 1968, 33, 2473

11 B Marsman and H Wynberg, 1 Org Chem , 1979, 44, 2312

6 (S H+)2- hydro, y -~-me lhy l' butanoie acid (AI·

amino-3-hydroxY lioline )

N- b.nzoyl (+)

Ph

HOOC + H CH(CH3 )2

1 O Cervinka, V Dudek and L Hub, Collect Czech Chern Cornrnun., 1970, 35, 724

2 C.c Tseng, S Terashima and S Yamada, Chern Pharrn Bull., 1977, 25, 29

3 1.1 Oh-Hashi and K Harada, Bull Chern Soc Jpn., 1966, 39, 2287

4 J.P Vigneron, M Dhaenens and A Horeau, Tetrahedron, 1977, 33, 507

5 G Li Bassi, P Ventura, R Monguzzi and G Pifferi, Gazz Chirn Ital., 1977, 107, 253

6 R.M Carman and J.J Kibby, Aust J Chern., 1976, 29, 1761

7 R.M Carman, C.J Hawkins and J.J Kibby, Aust J Chern., 1977, 30, 2465

8 H Redlich, J Xiang-Jun, H Paulsen and W Francke, Tetrahedron Leu., 1981, 5043

HOCH2"CrPh

13 (2S.4 SH +

)2-phenyl-I) 3-dioxolon-4-

),1-methanol CD ; I?]

dithiobisproponoic dislltlnobisproponoic di~,"nobisbutQnoic I

H2N+H • ~~) HzN+H • ;~] H 2 N+H !

CH~CH2 CHzCHzSMI CHzCHzSIMI

18, (2R ,4R)-(+) 2- phenyl)- ;3-(3-morcoplopropionyl)-

(2-hydro.y-thiozo5dine -4-corbollylic: acid

1 M Imuta and H Ziffer, J Org ehern., 1978, 43, 3530

2 H Nitsch and G Kresze, Angew ehern., Int Ed Engi., 1976, 15, 760

3 J.P Vigneron, M Qhaenens and A Horeau, Tetrahedron, 1977, 33, 507

4 R Zioudrou and P Chrysochou, Tetrahedron, 1977, 33, 2103

5 K Hintzer, R Weber and V Schurig, Tetrahedrun Lell., 1981, 55

H3C+H COOH

17 (2R,6SH 6-molhyl- 4-lhlahop-

)-2-omino-tOMdioic acid pt'opylcy t.in ,

(2-carboxy-(2R,4R)-ilomor 0100 [><&pd;

6 See p Al2

7 B Ringdahl, J.c Craig, A Fredga and W.A Bonner, Acta ehern Scand., Sero B, 1981, 35, 467, and refs therein

8 M.O Mack, R.R Hendrixson, R.A Palmer and R.G Ghirardelli, J Arn ehern Soc , 1976, 98, 7830

9 G Bettoni, C Franchini, R Perrone and V TortoreIla, Tetrahedron, 1980, 36, 409

10 A Afzali-Ardakani and H Rapoport, J Org ehern., 1980, 45, 4817

11 J.C Craig, S.c Lee, G Zdansky and A Fredga, J Arn ehern Soc., 1976, 98, 6456

12 R Parthasarathy, B Paul and W Korytynk, J Arn ehern Soc., 1976, 98, 6634

13 J.F Carson, J ehern Soc., Perkin Trans 1, 1977, 1964

14 M Oya, E Kato, J Iwao and N Yasuoka, ehern Pharrn Bull., 1982, 30, 484

(RH-);ndon-l'oI A2IJ.18

2 (RH+)benzsuberol

4 (RH-)2, 2 -dimelhyl- IJ (R)-(+)3,3-

dimothylpenlone-"'olrolol 1,2,5-lnol Sy AS(H)[/l

CI31 i [.1) CI!) OH &M ~[/l ~

cc> OH cO 'OH CO< MIooe)

8 (lS,2RH -)indone- 7 (lR,2RJ-{-)indone- 8 (R)-(-)2,2-dimolhyl- 9

(R)-(-)2-acoloxY'3,3- _ ~'3:d~~ _ _ _ 1 J 2-diol indan- t-ol dimethyl91utorie acid

di-Me ut.r

o={]

10 (SH+)ocloelolhopin 11 (RJ-{-)2-hydroxy-3,3-dimelhylsuccinic (R)-(-)ponloloclono

Abs X-roy [61 I oeld di-Mo o,'.r OA< (- ) T" 41 A':S 12

(1R,2SH+)I'phonyl-<orrespondi"'l aleohol [5], I I eocro.pondino 01_01 [5]

(SH-)llovanone A'9.18

14 (5 H-) Ilovon

A 1711

1 M Briancourt, J.P Guette and A Horeau, CR Hebd Seances Aead Sei., (e), 1972, 274, 1203, and refs therein

2 K Kabuto, M Imuta, E.S Kempner and H Ziffer, J Org ehern., 1978,43,2357

3 M Imuta and H Ziffer, J Org ehern., 1978, 43, 4540

4 E J Coreyand R.B Mitra, J Am ehern Soe., 1962, 84, 2938

5 I Muzart and J.P Pete, Tetrahedron Lett., 1977, 303

6 'A Jaunin, Tl Peteher and H.P Weber, J ehern Soe., Perkin Trans 2, 1977, 186

A 1811

CH 2 0H H+NH 2

(einie acid A '0 12 pnenylpyrrolidine-2,4- phen.,.lp)'rro~djne ,

6 (S)-(-)I-bon zyl- 3- 7 (SH+)3-phenyl· 8 (RH

-)phenyl-phenyl~iperidfne- piperidine i 9'ypho:5

(R)-(-)3-methyl-2-1,llIuoro-2 - phenyl- 2-phonylpropionlc acid ccid A41.12

14 (R)-(-)

2-(3-benzyl-phenyl)proplonic acid

COOH

~;i ptH PhCO CH]

18 (R)-( ) I-chloro- phenyl- 3-molhylbulon •

2-2 G Bettoni, C Franchini, F Morlacchi, N Tangari and V TortoreIla, J Org Chern., 1976, 41, 2780

3 See p ASO

4 D.L Dull, Diss Abstr., 1968, 29, 538B

5 J.C Craig, W.E Pereira, Jr., B Halpern and J.W Westley, Tetrahedron, 1971, 27, 1173

6 J.L Schmiegel, Diss Abstr., 1968, 28, 4507B

7 G Comisso, M Mihalic, F Kajfez, V Sunjic and G Snatzke, Gazz Chirn /tal., 1980, 110, 123

8 T Hayashi, M Fukushima, M Konishi and M Kumada, Tetrahedron Leu., 1980, 79

9 T.A Hamor, J Chern Soc., Perkin Trans 2, 1977, 643

anthracen- I- ol Ac(-) bromo·l, 2, J, 4 - tetro·

hyd rophe non rhrene

1 D.R Boyd, R.M.E Greene, J.D Neill, M.E Stubbs, H Yagi and D.M Jerina, J Chern Soc., Perkin Trans 1, 1981, 1477

2 K Kabuto, M Imuta, E.S Kempner and H Ziffer, J Org Chern , 1978, 43, 2357

3 D.R Boyd, J.D Neill and M.E Stubbs, Chern Cornrnun., 1977, 873

4 M Koreeda, M.N Akhtar, D.R Boyd, J.D Neill, D.T Gibson and D.M Jerina, J Org Chern., 1978,43, 1023

,p' Q

Sr : "'" I A'

~ CR)-(+17,S,9,lo- benzo[o)pyren- 8-01

,9,10,1l-[,.)

,,, (SS,9R >-Hben.[o]

ont hrQc'ene- 8 )

9-oxide

1 H Yagi, H Akagi, D.R Thakker, H.D Mah, M Koreeda and D.M Jerina, J Arn ehern Soc., 1977, 99, 2358

2 D.R Boyd, G.S Gadaginamath, R Hamilton, H Yagi and D.M Jerina, Tetrahedron Lett., 1978, 2487

3 K Nakanishi, H Kasai, H eho, R.G Harvey, A.M Jeffrey, K.W Jennette and I.B Weinstein, J Arn ehern Soc., 1977,99,

258

4 D.R Boyd, G.S Gadaginamath, A Kher, J.F Malone, H Yagi and D.M Jerina, J ehern Soc., Perkin Trans 1,1980,2112

5 D.R Boyd, K.A Dawson, G.S Gadaginamath, J.G Hamilton, J.F Malone and N.D Sharma, J ehern Soc., Perkin Trans 1,

1981, 94

telfotin-2-corboxylic acid Z §(SH+)cyelotrimothylene- 3 (S)-( )1-

omino-2-3 - phonyl- 2-lhiohydontoin (mo t hoxymet hyl)- 4 (R.,Rl-clemolüne Abs X-ray [5]

N

H

11

(2S,4R)-(-)4- corboxylic acid

(RH-)buton-2-01 A1.UI I (R)-(-)penton- 2 - ol i

acid phtholote(-l I A 8 7 ocid phlholole(-) i ~ s IN C / H O + :

.' ' ';. ""/~-'J CH= CH 2

H -,

1 S Terashima, S Jew and K Koga, Tetrahedron Leu., 1977, 4507

2 J.H Poupaert and G Lhoest, Bull Soc Chirn Belg., 1979, 339

3 D Enders and H Eichenauer, Tetrahedron Leu., 1977, 191

4 R Busson and H Vanderhaeghe, J Org Chern., 1978, 43, 4438

5 A Ebnöther and H-P Weber, Helv Chirn Acta, 1976, 59, 2462

H OH

14 (2S,3S)-(

)I-cyono-3 ,4- epllhiobuton- 2-01

R,I X-ray ~.JJ

6 M Asami, H Ohno, S Kobayashi and T Mukaiyama, Bull Chern Soc Jpn., 1978, SI, 1869

7 I.Z Siemion and T Wieland, Tetrahedron, 1977, 33, 155

8 T Murakami, S Kitagawa and M Hatano, Bull Chern Soc Jpn., 1976, 49, 2631

9 See p A17

10 T Wieland, D Schermer, G Rohr and H Faulstich, Justus Liebigs Ann Chern., 1977, 806

11 J.B Jones and H.M Schwartz, Can J Chern., 1981, SI, 1954

12 M.E Daxenbichler, C.H Van Etten and I.A Wolff, Biochernistry, 1965, 4, 318

13 R.B Bates, R.A Grady and T.C Sneath, J Org ehern., 1972, 37, 2145

15 (RH J

3-hydroxy-4-penteneni t nI8

A 2211

CI ass 2a, 3a

( ) ~ OMe -<:12) [6J (Sl-(-)3-metho,y- eyeloh ne A 18 9 1 (lS,2SH+J2-melho,y-

(lR,6S)(-l7-oxo-9-nonon-8-on8

•

(IR,2SH+l2-hydro,y-cyclohuanecorbO.KyttC

oeid EI Ier (+l

7 (I R,2S H+l 2-hydro.y· 8 _ (IR, 2S

H+l2-hydroxy-cyclopentonecorbO.lylie c)'cloh.x- 3- ne- acid ethyl uter carboxyllc acid

10

ClR,3R)-(-leyelopenlono-1)2 1 3- triol

I! (lR,2RH+)1- ydroxy- (SH-)bulone-I,2,4- 12 0R, 2S H - ll

-hyd,0.y-buton.-l,2,4- tr iccrb- triCQrboxylic acid butone-',2 ,4-

tri(orb-oxy lle (homoei lrie) acid A 28.10 oxyllc(homocil'ie) acid

)3,4,5-triocttoxyeyelohexonone (- ) Quinic acid A 28.2

1 J.B Kay and J.B Robinson, J Chern Soc (C), 1969, 248, and refs therein

2 A.A Barr, I Frencel and J.B Robinson, Can J Chern., 1977, 55, 4180

3 B.S Deol, D.D Ridley and G W Simpson, Aust J Chern., 1976, 29, 2459

4 J.B Robinson, J Pharrn Pharrnacol., 1970, 22, 222

5 A Febrer, P Gomis and J Pascual, An Quirn., 1964, 60, 671

6 J.E Faixat, A Febrer, and J Pascual, An Quirn., 1961, 57, 705

i

i

H5 eyclohoxonone 81 CD (tal

(S)-H3-(olhyllhia)-7 K Chilina, U Thomas, A.F Tucci, K.D McMichael and C.M.Stevens, Biochernistry, 1969, 8, 2846

8 See p A26

9 H Paulsen and O Brauer, Chern Ber 1977, 110, 331

10 S Colonna, J Hudec, G Gottarelli, P Maniani, G.P Spada and P Palmieri, J Chern Soc., Perkin Trans 2, 1982, 1327

8 (RH-)3-

bromopro-pant-I , 2- dial

O-isopropylidene (+)

9 (R)-(+)o,i ronemethonol (glycidol )

[5) c(2) [2) NH.Oq·l[I)[J') CHzOH CH2NH2 H+O

C(3) H+OH

" \\ (RH+) i.op<opyl - (5)-(+) t ,2-i.opropyl· 11 (5H-)3-omino- 12 (R)-(- )glycerol I'

"-S -N ideneglycerold.· ideneglycerol A 14 7 propon -I,2-diol looylote

-isobut y I suceinic (isobut '1 I ta r torie)

ocid A'I1.8 di-Me •• ter (+l

2'opimor (+) All O by AS (H)

ond chirol nmr [9]

(0) [8]

CH 2 0H (H3C)2CHCH2+ OH

1 J.e Sowden and H.O.L Fischer, J Arn Chern Soc., 1942, 64, 1291

2 P.R Bird and J.S Chadha, Tetrahedron Lett., 1966, 4541

[I)

3 E Abderhalden and E Eichwald, Ber., 1914, 47, 1856, 2880; 1915, 48, 1847

4 B Robinson, Chern Ind (London)., 1976, 652

5 H Jackson and B Robinson, Chern.-Bio/ Interact., 1976, 13, 193

6 See p A14

7 L.M Weinstock, D.M Mulvey and R Tull, J Org Chern., 1976, 41, 3121

8 D Behr, J Dahmen and K Leander, Acta Chern Scand Sero B, 1976, 30, 309, 903

19 (5)-( )piporo,on

9 R.W Gray, A Guggisberg, K.P Segebarth, M Hesse and H Schmidt, He/v Chirn Acta, 1977, 60 , 1304

10 W.L Nelson and T.R Burke, J Org Chern , 1978, 43, 3641

11 W.L Nelson and J.E Wennerstrom , Chern Cornrnun , 1976, 921

A 23"

(5H-)4-hydroxy-4-hexonOfc acid IGetane

dimelhylamino-! compd : (8) _ _ _ _ L _._._._._._._._._._._

1 W.H Pirkle, D.L Sikkenga and M.S Pavlin, J Org Chern., 1977, 42, 384

2 P.A Levene and J.B Haller, J Biol Chern., 1929, 83, 177

3 R.K Hili and R.M Carlson, J Arn Chern Soc., 1965, 87, 2772

4 H Numan, C.B Troostwijk, J.H Wieringa and H Wynberg, Tetrahedron Lett., 1977, 1761

5 D.A Lightner and W.M.D Wijekoon, J Org Chern., 1982, 47, 306

6 H Numan and H Wynberg, J Org Chern., 1978, 43, 2232

7 A Perales, M Martinez-Ripoll, J Fayos, C von Carstenn-Lichterfelde and M Fernandez, Acta Crysrallogr., Sect B., 1982,38,

2763

8 A.S Angeleni, S Marzocchi and G Scapini, Gazz Chirn Ital., 1977, 107, 421

Class 2a, 3a, 3b

8 (+) elomo.line Ab5 X-ro), [7 J i

1 E Friedrich and W Lutz, Angew Chern., [nt Ed EngI., 1977, 16, 413

2 T Ishida, Y Asakawa, M Okano and T Aratani, Tetrahedron Lett., 1977, 2437

17 (2R ,3R)-(-)

hep'odeeoM-1,2,3- trioarbc»:ylic

( norronviformie)ocid

3 K Mori, S Tamada, M Uchida, M Mizumachi, Y Tachibana and M Matsui, Tetrahedron, 1978, 34, 1901

4 K Kabuto, H Shindo and H Ziffer, J Org Chern., 1977, 42, 1742

5 H Ziffer, K Kabuto, D.T Gibson, V.M Kobal and D.M Jerina, Tetrahedron, 1977, 33, 2491 and refs therein

6 B Akermark Acta Chern Scand., 1967, 21, 589

7 A Terzis, Cryst Struct Cornrnun., 1978, 7, 91

(S)-H 2-melhyl Y' 4 (S)-(+) 2,6-dimethyl- !5 (R)(+ )6 hydroxy4

-butyroloc1one oc'-2-ena T U 10 [.J] methylheJconoic acid _

2 K Mori, T Suguro and S Masuda, Tetrahedron Leu., 1978, 3447

3 C CarJini, D Pini, O Bonrignori and P Neuenschwander, Gazz Chirn Ital., 1973, 103, 1297

4 See p Tl

(CH:z )~HM·2

5 G J Cernigliaro and P.J Kocienski, J Org Chern , 1977, 42, 3622

6 N Cohen, W.F Eichel, R.J Lopresti, C Neukom, and G Saucy, J Org Chern., 1976, 41, 3505, 3512

7 R Zell, Helv Chirn Acta, 1979, 62 , 474

8 c.G Overberger and H Kaye , J Am Chern Soc., 1967, 89, 5640

Class 3a

5-dimothyl-6 (R) 5-mothy 2-en-l-one

lcyclohu-(+) in rtl [.5], ;x,;

H in rll [4] C(2)

[I)

c)'eloh ne A' 24 3

(RH+)-I,3-dimothyl-(RH+)3- cyclohlxonone A3B 4

mlthyl-O C(2)

" CH " " [ , ]

3 (RH ) 3- methyl-

cyelol"lexlnl

(RH-) huanono A 3B 12 ' [41 A' 24 10 co L

(1S,2RH+)2-othyl-cU) (gf"

(R)-(+)cycloh -3- 12 (RH+)3-cyclo- 13

(RH+)4-isopropenyl-~m.- ,-c,orboxylic ocid hexenyl methyl Ion cyclohlxln • A2B 1 1

1 C.l Cheer and C Djerassi, Tetrahedron LeU., 1976, 3877

2 J.B Jones and T Takemura, Can J Chern., 1982, 60, 2950

3 l.K Whitesell and S.W Feiman, J Org Chern., 1977,42, 1663

4 E Friedrich and W Lutz, Angew Chern., Int Ed Eng/., 1977, 16, 413

5 W Oppolzer and M Petrzilka, He/v Chirn Acta, 1978, 61, 2755

3 (IR, 3RH+) diml lhylcyclohuonl

1,3-(RH+) 4 cyclohlXfnl A2B t3

-mlthyl-B (RH+)6-methyl' cyclohex-2-en-'-onr

(25,65)-(+)2,6-CU) [e]

CH 3 H+NH2

(CH 2)3CH 3

14

(5H+)2-hlllylomin •

KI9 B

6 M Mousseron and M Paulet, Perfurnerie Mod., 1939,33, 101; Chern Zentra/b/., 1940, H, 895

7 H.L Goering, W.W Schmidt and V.D Singleton, J Org Chern., 1979,44,2282

8 R Perrone and V TortoreIla, Tetrahedron, 1978, 34, 2533

9 0 Ceder and H.G Nilsson, Acta Chern Scand., Sero B., 1976, 30, 908

10 C Djerassi, c.L vanAntwerp and P Sundararaman, Tetrahedron Leu., 1978, 535

(S)-3-oxooyclohoxoneprop-(in ral [t), (-)(In rol l2Jl

1 H Gerlach, Helv Chim Acta, 1978, 61, 2773

2 M Nakazaki, K Naemura and S Nakahara, Chem Commun., 1979, 82

3 A Numata, T Suzuki, K Ono and S Ueo, Yakugaku Zasshi, 1968, 88, 1198

4 L.H Schwartz and B.l Bathija, J Am Chem Soc , 1976, 98, 5344

5 M Nakazaki, K Yamamoto and M Maeda, J Org Chem., 1980, 45, 3229

Class 3a

(1S,2SH+)2-hydro.y-cyc!opentoneocltic 10 ClS,2SH+}-2-(2-hydro- 11 (RH+)2-mothyl-

(S)-(+)1,3-'Yllhyl )cycloponlanol cyclobulanono dibromobuta

12 (lR,4Sl-(-)4 -nolrahy- 13 (IR,3SH+)cyclopenl - 4- (IR,2R)+')cyclopenl' 14 (IR,2R)-(-)bi"(hydro- 1

dropyronylo.yr2 ono-l,3-dioI ' · benzoolt I ono-I, 2'd,corboxyllc 'ymothyl)cycl_ntono !

L D Varech, C Ouannes and J Jacques, Bull SOC Chirn Fr., 1965, 1662

2 A.J ITWin and J.B Jones, J Arn Chern Soc., 1977,99, 1625

3 S Terashima, S Yamada and M Nara, Tetrahedron Leu., 1977, 1001

(RH-) cyclopontanono

2·molhyl-A'2~ IO

4 D van Leusen, P.H.F.M Rouwette and A.M van Leusen, J Org Chern., 1981, 46, 5159

5 W.J Richter and B Richter, Isr J Chern., 1976, 15, 57

6 J Fried, C Lin, M Mehra, W Kao and P Dalven, Ann N Y Acad Sci., 1971, 180, 38

[6]

18

(R)-(-)2-octyI-cyclopentononl

(3R,4RJ-H3,4-o 'CH,

2 (RH +) 3- p.nt.n • ' " [2] C( 211[/]

mofhylcyclo-C(51~

o-CH3

\CH ,

3 dimllhyleycloponlone

)2-cyclop""ton-'-eH, (RH+)3·molhyl-

1 V Schurig, Angew Chern., Int Ed Eng/., 1977, 16, 110

2 G.D Andrews and J.E Baldwin, 1 Arn Chern Soc., 1976, 98, 6705

3 S Takano, K Masuda and K Ogasawara, Heterocycles, 1981, 16, 1509

4 R.K Hili and A.G Edwards, Tetrahedron Leu., 1964, 3239

5 W.J Richter and B Richter, Isr J Chern., 1976, 15, 57

6 S.F Birch and R.A Dean, J Chern Soc., 1953, 2477

7 H Kuritani, Y Takaoka and K Shingu, J Org Chern., 1979, 44, 452

CMo 3 , 7.§( 15, 2R, 4S)-(-) 2-

R.3R)-(-)cydop""tane-oOH

"CI"~H

7 (hydro.ym.! hyl) cyelo p.ntane,

(lR,3RH+)1.3-bi.-o "CH3

10 (lR,3R dimethylc)'clopentane

)(+)1.3-14 (IR,3R)-(+)I melhyl- 3- melhyleyolo-

-nydro.y-pen tane ,

18 (IR 3R )- ( )3- mel hyl' eyelopentonecorboxylic ocod

8 5-1"'" bulyloyoloho xonono

'h1ucoe corboxyllc aCId

1 C Djerassi, E.J Warawa, R.E Wolff and E.J Eisenbraun, J Org., 1960, 25, 917

2 M Tichy, P Malon, I Fric and K Blaha, Collect Czech Chern Cornrnun., 1977, 42, 3591

3 C Beard, C Djerassi, J Sicher, F Sipos and M Tichy, Tetrahedron, 1963, 19, 919

4 G BeUucci, G Ingrosso, A Marsili, E Mastrorilli and I Moretti, J Org Chern., 1977, 42, 1079

5 S.K Sadozai, J.A Lepoivre, R.A Dommisse and F.C Alderweireldt, Bull Soc Chirn Belg., 1980, 89, 637

6 A.K MacBeth and J.A Mills, J Chern Soc., 1947, 205

7 c.G Overberger and H Kaye, J Am Chern Soc , 1967, 89, 5640

8 W Hückel and K.-D Thomas, Justus Liebigs Ann Chern., 1961, 645, 177

9 M.S Silver and T Sone, J Am Chern Soc., 1968, 90, 6193

10 H.G.W Leuenberger, W Boguth, E Widmer and R Zell, He/v Chirn Acta, 1976, 59, 1832

I (SH+)I-ha'a-2- 2 (R)-(+)3-methyl- (S)-(+) '-ha'a- 2 -

methy'-butane A 27 11 3 (SH+)5-methy'-hept-t - yne

ethylhexonu( X::: Br,IL hepton-3-ol

CH(COOEt )2

~C+H

CHzCHO

9 (S )-(+)4,4-bi earbanyl)- 3-methylbu'anal

13 (S H+)6-mothyloet-l-on • • 4 (SH+)6-molt1yloe.· (SH+)3-mothyl- 1:1 (SJ-(+) 6 -molt1yloeton- I

'-yno oetano A 27 • 3 2-an I

1 R.L Burwell and G.S Gordon, J Am Chern Soc., 1948, 70, 3128

2 K.B Wiberg and G Foster, J Am Chern_ Soc., 1961, 83, 423

3 H Schechter and D.K Brain, J Am Chern Soc., 1963, 85, 1806

4 L Lardicci, C Botteghi and E Belgodere, Gazz Chirn Ital., 1967, 'Y1, 610

5 L Lardicci, C Botteghi and E Benedetti, J Org Chern., 1966, 31, 1534

6 J Kenyon and RC Platt, J Chern Soc., 1939, 633

7 S_ Hashimoto, N_ Komeshima, S Yamada and K Koga, Chern Pharm Bull., 1979, 27, 2437

8 P Salvadori, S Bertozzi and R Lazzaroni, Tetrahedron Lett., 1977, 195

Class 3a

t t

(3S,85)-(+)3,8-dimlthyldlconl