A Concise Synthesis of (-)-Aplyviolene Facilitated by a Strategic Tertiary Radical Conjugate Addition

被引：224
作者：
Schnermann, Martin J. [1 ]
Overman, Larry E. [1 ]
机构：
[1] Univ Calif Irvine, Dept Chem, Irvine, CA 92697 USA
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2012年 / 51卷 / 38期
关键词：
fragment-coupling; fused-ring systems; photoredox chemistry; terpenoids; total synthesis; ENANTIOSELECTIVE TOTAL-SYNTHESIS; VISIBLE-LIGHT PHOTOCATALYSIS; PHOTOREDOX CATALYSIS; PHOTOSENSITIZED DECARBOXYLATION; N-(ACYLOXY)PHTHALIMIDES; STEREOSELECTIVITY; APLYVIOLENE; SELECTIVITY; REAGENT; ESTERS;
D O I：
10.1002/anie.201204977
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A second-generation synthesis of the rearranged spongian diterpene aplyviolene is reported. The key step is the addition of a trialkyl tertiary radical generated by photoredox-mediated fragmentation of a N-(acyloxy) phthalimide to an α-chloropentenone (see scheme). This process fashioned a quaternary stereocenter while combining two units of significant complexity. Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码：9576 / 9580
页数：5
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