Total synthesis of racemic lasidiol via intramolecular [4+3] cycloaddition

被引：18

作者：

Kreiselmeier, G ^{[1
]}

Föhlisch, B ^{[1
]}

机构：

[1] Univ Stuttgart, Inst Organ Chem & Isotopenforsch, D-70569 Stuttgart, Germany

来源：

TETRAHEDRON LETTERS | 2000年 / 41卷 / 09期

关键词：

D O I：

10.1016/S0040-4039(99)02296-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Lasidiol, a sesquiterpenoid with a carotane skeleton, and its 8a-epimer have been synthesized in 12 steps starting from 2-methylfuran. Key elements in the synthesis are constructions of the carbon framework in an intramolecular [4+3] cycloaddition and cleavage of the epoxy-bridge by reductive elimination with sodium naphthalenide after reduction and hydrogenation of the bromo-substituted cycloadducts. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：1375 / 1379

页数：5

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