An asymmetric synthesis of the BC ring system of 8-epitaxoids by way of intramolecular aldol and successive stereoselective methylation reactions

被引：13

作者：

Mukaiyama, T

Shiina, I

Iwadare, H

Saitoh, M

Nishimura, K

Nishimura, T

Ohkawa, N

Sakoh, H

Saitoh, K

机构：

[1] Department of Applied Chemistry, Faculty of Science, Science University of Tokyo, Tokyo 162, Kagurazaka, Shinjuku-ku

来源：

CHEMISTRY LETTERS | 1996年 / 06期

关键词：

D O I：

10.1246/cl.1996.483

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Optically active 1 alpha-allyl-1 beta,11 beta-benzylidenedioxy-2 alpha,10 beta-bis(benzyloxy)-7 beta,9 beta-isopropylidenedioxy-8 alpha,12,12-trimethyl-4-methylenebicyclo[6.4.0]dodecane (2)(1) which corresponds to BC ring system of 8-epitaxoids was prepared in high yield from ketoaldehyde 8 via intramolecular aldol cyclization and successive stereoselective methylation reactions. The ketoaldehyde 8 was synthesized from 8-membered ring compound 3 by stereoselective Michael addition using higher-order cuprate.

引用

页码：483 / 484

页数：2

共 15 条

[1] SYNTHESIS APPLICATIONS OF CATIONIC AZA-COPE REARRANGEMENTS .24. THE AZA-COPE-MANNICH APPROACH TO STRYCHNOS ALKALOIDS - SHORT STEREOCONTROLLED TOTAL SYNTHESES OF (+/-)-DEHYDROTUBIFOLINE AND (+/-)-AKUAMMICINE [J].

ANGLE, SR ;

FEVIG, JM ;

KNIGHT, SD ;

MARQUIS, RW ;

OVERMAN, LE .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (10) :3966-3976

[2] SYNTHESIS APPLICATIONS OF CATIONIC AZA-COPE REARRANGEMENTS .22. NEW APPROACH TO STRYCHNOS ALKALOIDS - STEREOCONTROLLED TOTAL SYNTHESIS OF (+/-)-DEHYDROTUBIFOLINE [J].

FEVIG, JM ;

MARQUIS, RW ;

OVERMAN, LE .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (13) :5085-5086

[3]

FICINI J, 1977, TETRAHEDRON LETT, P1081

[4] ENONES WITH STRAINED DOUBLE-BONDS .4. THE BICYCLO[5.3.1]UNDECANE SYSTEM [J].

HOUSE, HO ;

SIELOFF, RF ;

LEE, TV ;

DETAR, MB .

JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (10) :1800-1806

[5]

KINGSTON DGI, 1993, PROG CHEM ORG NAT PR, V61, P1

[6] SYNTHESIS APPLICATIONS OF CATIONIC AZA-COPE REARRANGEMENTS .28. ASYMMETRIC TOTAL SYNTHESES OF (-)-STRYCHNINE AND (+)-STRYCHNINE AND THE WIELAND-GUMLICH ALDEHYDE [J].

KNIGHT, SD ;

OVERMAN, LE ;

PAIRAUDEAU, G .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (21) :5776-5788

[7] A CONCISE SYNTHESIS OF (+/-)CHOKOL-A [J].

LAWLER, DM ;

SIMPKINS, NS .

TETRAHEDRON LETTERS, 1988, 29 (10) :1207-1208

[8]

MUJAIYAMA T, 1995, CHEM LETT, P229

[9] A NOVEL-APPROACH TO THE SYNTHESIS OF TAXOL - A SYNTHESIS OF OPTICALLY-ACTIVE 3,7-DIBENZYLOXY-4,8-DI-T-BUTYL-DIMETHYLSILOXY-5,5-DIMETHYL-6-P-METHOXYBENZYLOXY-2-OCTANONE BY WAY OF STEREOSELECTIVE ALDOL REACTIONS [J].

MUKAIYAMA, T ;

SHIINA, I ;

SAKATA, K ;

EMURA, T ;

SETO, K ;

SAITOH, M .

CHEMISTRY LETTERS, 1995, (03) :179-180

[10] EVALUATION OF D-RIBOSE AS AN ENANTIOPURE BUILDING-BLOCK FOR CONSTRUCTION OF THE C-RING OF TAXOL AND ITS CONGENERS [J].

PAQUETTE, LA ;

BAILEY, S .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (24) :7849-7856

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