TOTAL SYNTHESIS OF (+/-)-AFRICANOL AND (+/-)-ISOAFRICANOL

被引：29

作者：

FAN, WM ^{[1
]}

WHITE, JB ^{[1
]}

机构：

[1] UNIV TEXAS,DEPT CHEM,BOX 19065,ARLINGTON,TX 76019

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1993年 / 58卷 / 13期

关键词：

D O I：

10.1021/jo00065a018

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A six-step synthesis of the sesquiterpenes africanol and isoafricanol from 3,5,5-trimethylcyclohex-2-en-1-one is reported. The anionic oxy-Cope rearrangement is used to prepare substituted 5-cyclodecenones functionalized with an allylstannane moiety, which, upon cyclization with the ketone, lead to hydroazulene derivatives. The stereochemistry in the transannular cyclization can be controlled through the choice of reaction conditions both with respect to the ring fusion itself and with respect to a preexisting chiral center. Cyclopropanation of the alkene that is generated following cyclization completes the synthesis of both compounds.

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页码：3557 / 3562

页数：6

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