Ultrasound assisted reductive cleavage of eudesmane and guaiane γ-enonelactones.: Synthesis of 1α,7α,10αH-guaian-4,11-dien-3-one and hydrocolorenone from santonin

被引：28

作者：

Blay, G ^{[1
]}

Bargues, V ^{[1
]}

Cardona, L ^{[1
]}

García, B ^{[1
]}

Pedro, JR ^{[1
]}

机构：

[1] Univ Valencia, Fac Quim, Dept Quim Organ, E-46100 Burjassot, Valencia, Spain

来源：

TETRAHEDRON | 2001年 / 57卷 / 48期

关键词：

sonochemistry; cleavage reaction; terpenes; lactones;

D O I：

10.1016/S0040-4020(01)00986-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Ultrasound enhances the rate of reductive cleavage of the C-6-oxygen bond of sesquiterpene enonelactones. trans-Eudesmanolides 1c-1g, cis-eudesmanolides 2a-2c, and trans-guaianolides 4a-4d react with Zn in acetic acid-H2O under sonochemical conditions to afford the corresponding sesquiterpene. acids 3a-3g and 5a-5d, respectively in good yields. Starting from 5d two natural guaianes 1 alpha ,7 alpha ,10 alphaH-guaian-4, 11-dien-3-one (6) and hydrocolorenone (7) have been prepared in good yields through a straightforward sequence. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：9719 / 9725

页数：7

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