DECONJUGATION OF ALPHA,BETA-UNSATURATED ESTERS AND AN INTRAMOLECULAR MICHAEL REACTION OF BIS-ALPHA,BETA-UNSATURATED ESTERS WITH TRIALKYLSILYL TRIFLUOROMETHANESULFONATE IN THE PRESENCE OF TERTIARY AMINE - SYNTHESIS OF (PLUS-OR-MINUS)-RICCIOCARPIN-A

被引：34

作者：

IHARA, M ^{[1
]}

SUZUKI, S ^{[1
]}

TANIGUCHI, N ^{[1
]}

FUKUMOTO, K ^{[1
]}

机构：

[1] TOHOKU UNIV, INST PHARMACEUT, SENDAI, MIYAGI 980, JAPAN

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1993年 / 19期

关键词：

D O I：

10.1039/p19930002251

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Treatment of the alpha,beta-unsaturated esters 1, 6 and 8 with trialkylsilyl trifluoromethanesulfonate in the presence of a tertiary amine gave, via silyl dienol ethers, the corresponding deconjugated esters 3, 7 and 9 as the major products, respectively. Reaction of bis-alpha,beta-unsaturated esters 12a and 12b with a trialkylsilyl trifluoromethansulfonate in the presence of a tertiary amine caused an intramolecular Michael reaction to produce the cyclopentanes 14a and 20a and the cyclohexanes 14b and 20b. Bicyclic compounds 21a and 21b formed by tandem Michael-Dieckmann or intramolecular Diels-Alder reaction were concurrently obtained. The cyclohexane derivative 14b was converted into the racemate of a sesquiterpene, (+/-)-ricciocarpin A 22.

引用

页码：2251 / 2258

页数：8

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