DIASTEREOSELECTIVE 1,4-ADDITION OF VARIOUS NUCLEOPHILES TO 5-TRIMETHYLSILYL-2-CYCLOHEXENONE - SYNTHESIS OF (+)-RAMULOSIN

被引：17

作者：

ASAOKA, M

SONODA, S

FUJII, N

TAKEI, H

机构：

[1] Department of Life Chemistry, Tokyo Institute of Technology, Midori-ku, Yokohama, 227, Nagatsuta

来源：

TETRAHEDRON | 1990年 / 46卷 / 05期

关键词：

D O I：

10.1016/S0040-4020(01)81963-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Base catalyzed reaction of active methylene compounds or oxygen catalyzed reaction of trialkylboranes via radical pathway with 5-trimethylsilyl-2-cyclohexenone (1) gave the corresponding products with modest to high (3:2- 20:1) diastereopurities. High diastereoselectivity (6:1- > 20:1) was observed in the reactions of enol silyl ethers, allylsilanes, hydrogenperoxide, and diethylaluminium cyanide with 1 and its 3-substituted derivatives. Full details of the total synthesis of (+)-ramulosin utilizing the diastereospecific product are also described. © 1990.

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页码：1541 / 1552

页数：12

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