INTRAMOLECULAR ADDITIONS OF ALLYLSILANES TO CONJUGATED DIENONES - DIRECT STEREOSELECTIVE SYNTHESES OF (+/-)-NEOLEMNANYL ACETATE AND (+/-)-NEOLEMNANE

被引：30

作者：

MAJETICH, G

LOWERY, D

KHETANI, V

SONG, JS

HULL, K

RINGOLD, C

机构：

[1] Department of Chemistry, The University of Georgia, Athens

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1991年 / 56卷 / 12期

关键词：

D O I：

10.1021/jo00012a036

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The total synthesis of the marine sesquiterpenes neolemnanyl acetate (1) and neolemnane (2) is reported. An intramolecular allylsilane addition to a conjugated dienone is used to assemble the basic 6,8-fused skeleton. Functionalization of the cyclooctane ring was achieved by means of a regiospecific photooxygenation.

引用

页码：3988 / 4001

页数：14

共 105 条

[1]

ARVINITIS A, 1989, J AM CHEM SOC, V111, P2737

[2] SELECTIVE HYDROLYSIS OF ALPHA,BETA-UNSATURATED AND BETA,GAMMA-UNSATURATED KETALS - METHOD FOR DECONJUGATION OF BETA,BETA-DISUBSTITUTED ALPHA,BETA-UNSATURATED KETONES [J].