Novel methoxyl and hydroxyl directed pinacol rearrangements of an isocaryolane sesquiterpenoid under mitsunobu conditions

被引：6

作者：

Collado, IG

Hanson, JR

Hernández-Galán, R

Hitchcock, PB

Macías-Sánchez, AJ

Racero, JC

机构：

[1] Univ Cadiz, Fac Ciencias, Dept Quim Organ, Cadiz 11510, Spain

[2] Univ Sussex, Sch Chem Phys & Environm Sci, Brighton BN1 9QJ, E Sussex, England

来源：

TETRAHEDRON LETTERS | 1999年 / 40卷 / 35期

关键词：

Mitsunobu reactions; rearrangements; Botrytis cinerea; antifungals;

D O I：

10.1016/S0040-4039(99)01335-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Treatment of 8-methoxy-isocaryolan-9 alpha-ol (1) with acid on the one hand and with diethyl azodicarboxylate (DEAD)/triphenylphosphine on the other, leads to different pinacol rearrangements of the isocaryolane skeleton. 1S,2S,5R,9R-8-oxo-1,4,4-trimethyltricyclo[7.2.1.0(2,5)]dodecane (2), which possesses a novel sesquiterpenoid skeleton, was obtained under Mitsunobu conditions. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

收藏

页码：6497 / 6498

页数：2

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