Interplay of Cascade Oxidative Cyclization and Hydride Shifts in the Synthesis of the ABC Spiroketal Ring System of Pectenotoxin-4

被引：26

作者：

Donohoe, Timothy J. ^{[1
]}

Lipinski, Radoslaw M. ^{[1
]}

机构：

[1] Univ Oxford, Dept Chem, Chem Res Lab, Oxford OX1 3TA, England

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2013年 / 52卷 / 09期

关键词：

catalysis; cyclization; natural products; pectenotoxin; spiroketals; STEREOCONTROLLED CYCLIZATION; ASYMMETRIC SYNTHESES; TETRAHYDROFURANS; FRAGMENT; 1,5-DIENES; APOPTOSIS; STRATEGY; SUBUNIT; FORM;

D O I：

10.1002/anie.201208919

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Concepts: The formation of stereochemically defined bis-THF units through a double cyclization and a hydride-shift-initiated route to spiroketals is described (see scheme; Xc=chiral auxiliary). The resulting sequence has been used in a synthesis of the C1-16 fragment of the naturally occurring antitumor agent pectenotoxin-4. Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：2491 / 2494

页数：4

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