On the regioselectivity of the Baeyer-Villiger reaction of 2,6-dialkyl cyclohexanones: Application to the synthesis of sordidin, a male pheromone emitted by Cosmopolites sordidus

被引：16

作者：

Beauhaire, J ^{[1
]}

Ducrot, PH ^{[1
]}

机构：

[1] INRA,UNITE PHYTOPHARM & MEDIATEURS CHIM,F-78026 VERSAILLES,FRANCE

来源：

BIOORGANIC & MEDICINAL CHEMISTRY | 1996年 / 4卷 / 03期

关键词：

Cosmopolites sordidus; regioselective Baeyer-Villiger reaction; tetrasubstituted cyclohexanone; caprolactone;

D O I：

10.1016/0968-0896(96)00019-3

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

The diastereoselective synthesis of (1S*,3R*,5R*,7S*)-2,8-dioxa-1-ethyl-3,5,7-trimethylbicyclo[3.2.1]octane (1d) has been achieved using as the key step the regioselective Baeyer-Villiger reaction of 2,6-disubstituted cyclohexanone. Copyright (C) 1996 Elsevier Science Ltd

引用

页码：413 / 418

页数：6

共 6 条

[1] IDENTIFICATION AND SYNTHESIS OF SORDIDIN, A MALE PHEROMONE EMITTED BY COSMOPOLITES-SORDIDUS [J].

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DUCROT, PH ;

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ROCHAT, D ;

NDIEGE, IO ;

OTIENO, DO .

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[2] EVIDENCE FOR VOLATILE MALE-PRODUCED PHEROMONE IN BANANA WEEVIL COSMOPOLITES-SORDIDUS [J].

BUDENBERG, WJ ;

NDIEGE, IO ;

KARAGO, FW .

JOURNAL OF CHEMICAL ECOLOGY, 1993, 19 (09) :1905-1916

[3] REGIOSELECTIVE BAEYER-VILLIGER REACTION OF POLYHYDROXYCYCLOHEXANONE DERIVATIVES [J].

CHIDA, N ;

TOBE, T ;

OGAWA, S .

TETRAHEDRON LETTERS, 1994, 35 (39) :7249-7252

[4]

Krow G.R., 1993, ORGANIC REACTIONS, V43, P251, DOI DOI 10.1002/0471264180.OR043.03

[5] CONFORMATIONAL PREFERENCES IN HEXAHYDRO-2H-AZEPIN-2-ONES (CAPROLACTAMS) [J].

MATALLANA, A ;

KRUGER, AW ;

KINGSBURY, CA .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (11) :3020-3025

[6]

MORI K, 1986, TETRAHEDRON, V42, P5545, DOI 10.1016/S0040-4020(01)88158-8

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