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.
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收藏
页码：2491 / 2494
页数：4
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