CONVERSION OF SANDARACOPIMARIC ACID INTO AN ANDROSTANE ANALOG STEROID

被引：14

作者：

ABAD, A

AGULLO, C

ARNO, M

DOMINGO, LR

ZARAGOZA, RJ

机构：

[1] Departamento de Quimica Organica, Universidad de Valencia, Valencia, Dr. Moliner 50

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1990年 / 55卷 / 08期

关键词：

D O I：

10.1021/jo00295a026

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The conversion of the diterpenoid resin acid, sandaracopimaric acid la, into a tetracyclic system of steroid is described. Key steps for the construction of the D ring are reductive nucleophilic acylation of ketone 5 and intramolecular aldol condensation of keto aldehyde 10. Various unsuccessful attempted methods for achieving the one-carbon homologation of the C-14 carbonyl group of 5 are described. © 1990, American Chemical Society. All rights reserved.

引用

页码：2369 / 2373

页数：5

共 30 条

[1] SYNTHESIS OF (+)-PODOCARP-8(14)-EN-13-ONE AND METHYL-(+)-13-OXO-PODOCARP-8(14)-EN-18-OATE FROM ABIETIC ACID
ABAD, A
ARNO, M
DOMINGO, LR
ZARAGOZA, RJ
[J]. TETRAHEDRON, 1985, 41 (21) : 4937 - 4940
[2] 4-CARBOMETHOXY-5ALPHA-ANDROSTANE DERIVATIVES - SYNTHESIS OF (-)-SANDARACOPIMARIC ACID
AFONSO, A
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1970, 35 (06) : 1949 - &
[3] DITERPENE CHEMISTRY .4. OXYMERCURATION-DEMERCURATION OF METHYL PIMARATE AND METHYL SANDARACOPIMARATE
APSIMON, JW
KREHM, H
[J]. CANADIAN JOURNAL OF CHEMISTRY, 1969, 47 (15): : 2865 - &
[4] DEHYDROBROMINATION OF METHYL II ALPHA-BROMO-12-OXOPODOCARPAN-19-OATE
BELL, RA
GRAVESTO.MB
[J]. CANADIAN JOURNAL OF CHEMISTRY, 1969, 47 (19): : 3661 - &
[5] BERMEJO F, 1988, CAN J CHEM, V66, P2200
[6] RESEARCHES ON ACETYLENIC COMPOUNDS .1. THE PREPARATION OF ACETYLENIC KETONES BY OXIDATION OF ACETYLENIC CARBINOLS AND GLYCOLS
BOWDEN, K
HEILBRON, IM
JONES, ERH
WEEDON, BCL
[J]. JOURNAL OF THE CHEMICAL SOCIETY, 1946, (JAN): : 39 - 45
[7] STRUCTURE AND STEREOCHEMISTRY OF REDUCTION PRODUCTS OF ABIETIC-TYPE RESIN ACIDS
BURGSTAH.AW
MARX, JN
ZINKEL, DF
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1969, 34 (06) : 1550 - +
[8] SILICON IN SYNTHESIS .18. SYNTHESIS OF METHYL KETONES AND (R)-(+)-FRONTALIN USING (1-CHLORO-1-(TRIMETHYLSILYL)ETHYL)LITHIUM FOR THE DIRECT CONVERSION OF ALDEHYDES AND KETONES INTO ALPHA,BETA-EPOXY TRIMETHYLSILANES
COOKE, F
ROY, G
MAGNUS, P
[J]. ORGANOMETALLICS, 1982, 1 (07) : 893 - 897
[9] DIMETHYLOXOSULFONIUM METHYLIDE ((CH3)2SOCH2) AND DIMETHYLSULFONIUM METHYLIDE ((CH3)2SCH2) FORMATION AND APPLICATION TO ORGANIC SYNTHESIS
COREY, EJ
CHAYKOVSKY, M
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1965, 87 (06) : 1353 - +
[10] PROTECTION OF HYDROXYL GROUPS AS TERT-BUTYLDIMETHYLSILYL DERIVATIVES
COREY, EJ
VENKATESWARLU, A
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1972, 94 (17) : 6190 - +

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