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 4 条

[1] IDENTIFICATION AND SYNTHESIS OF SORDIDIN, A MALE PHEROMONE EMITTED BY COSMOPOLITES-SORDIDUS
BEAUHAIRE, J
DUCROT, PH
MALOSSE, C
ROCHAT, D
NDIEGE, IO
OTIENO, DO
TETRAHEDRON LETTERS, 1995, 36 (07) : 1043 - 1046
[2] Efficient synthesis of sordidin, a male pheromone compound emitted by Cosmopolites sordidus.
Ducrot, PH
SYNTHETIC COMMUNICATIONS, 1996, 26 (21) : 3923 - 3928
[3] Access to 1,2,3,4-Tetraoxygenated Benzenes via a Double Baeyer-Villiger Reaction of Quinizarin Dimethyl Ether: Application to the Synthesis of Bioactive Natural Products from Antrodia camphorata
Newson, Harriet L.
Wild, Duncan A.
Yeung, Sing Yee
Skelton, Brian W.
Flematti, Gavin R.
Allan, Jane E.
Piggott, Matthew J.
JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (08): : 3127 - 3135
[4] Synthesis and crystal structure of bis-[(4S,5S)-4,5-dihydro-4,5-diphenyl-2-(2′-oxidophenyl-χO)oxazole-χN] copper(II) and its application in the asymmetric Baeyer-Villiger reaction
Peng, YG
Feng, XM
Yu, KB
Li, Z
Jiang, YZ
Yeung, CH
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2001, 619 (1-2) : 204 - 208

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