Studies on the synthesis of Schisandraceae natural products: Exploring a cyclopropylcarbinol ring expansion strategy

被引：32

作者：

Fischer, Derek ^{[1
]}

Theodorakis, Emmanuel A. ^{[1
]}

机构：

[1] Univ Calif San Diego, Dept Chem & Biochem, La Jolla, CA 92093 USA

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2007年 / 2007卷 / 25期

关键词：

synthesis design; cyclopropanation; synthetic methods; Baeyer-Villiger oxidation; ring expansion;

D O I：

10.1002/ejoc.200700336

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Acid mediated cyclopropylcarbinol ring expansion has been shown to be a viable method for the construction of the AB ring framework of lancifodilactone F and related terpenoids of the Schisandraceae family of natural products. We found that this rearrangement proceeds with good stereochemical control based on inversion of the C10 cyclopropyl center. Our studies indicate that the cis-decalin motif of 31 could be used as a key synthetic precursor of certain Schisandraceae metabolites. ((c) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007).

引用

页码：4193 / 4196

页数：4

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