The synthesis of Ambra oxide related compounds starting from (+)-larixol. Part 3

被引：14

作者：

Bolster, MG ^{[1
]}

Jansen, BJM ^{[1
]}

de Groot, A ^{[1
]}

机构：

[1] Wageningen Univ, Organ Chem Lab, NL-6703 HB Wageningen, Netherlands

来源：

TETRAHEDRON | 2002年 / 58卷 / 26期

关键词：

larixol; stereoselective enone reduction; intramolecular etherification; Ambra oxide;

D O I：

10.1016/S0040-4020(02)00494-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

(+)-Larixol can be easily transformed into intermediates with an hydroxyl group at C(6), a Delta(7) double bond and a substituted side chain at C(9) with a second hydroxyl group. Abstraction of the allylic hydroxyl group at C(6), followed by interception of the resulting mesomeric carbocation at C(8) by the hydroxyl group in the side chain, allows the synthesis of some C(13) modified Delta(6) tricyclic tetrahydropyranyl ethers (Delta(6)-Ambra oxides). The formation of Delta(6,8)-dienes proves to be a seriously competing reaction. (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

页码：5275 / 5285

页数：11

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