Asymmetric total synthesis of the indole alkaloid cyclopiazonic acid and first structure activity data

被引：21

作者：

Beyer, W. R. Christian ^{[1
]}

Woithe, Katharina ^{[2
]}

Lueke, Bettina ^{[2
]}

Schindler, Michael ^{[2
]}

Antonicek, Horst ^{[2
]}

Scherkenbeck, Juergen ^{[1
]}

机构：

[1] Berg Univ Wuppertal, Fachgrp Chem, D-42119 Wuppertal, Germany

[2] Bayer CropSci AG, D-40789 Monheim, Germany

来源：

TETRAHEDRON | 2011年 / 67卷 / 17期

关键词：

Indole alkaloid; Cyclopiazonic acid; SERCA; Enantioselective synthesis; Structure-activity data; TETRAMIC ACIDS; CA2+ PUMP; CA2+-ATPASE; THAPSIGARGIN; SENSITIVITY; ROUTE; CELLS;

D O I：

10.1016/j.tet.2011.03.002

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The indole alkaloid cz-cyclopiazonic acid (CPA) is one of the few known inhibitors of sarco(endo)plasmic reticulum Ca2+-ATPase (SERCA) besides the terpenoids thapsigargin and artemisinin. We report here the first asymmetric total synthesis of cyclopiazonic acid by a modification of the Knight synthesis, currently the most efficient route to CPA. First structure activity data of CPA derivatives and stereoisomers are presented and will be discussed in connection with the published crystal-structures of CPA SERCA complexes. (C) 2011 Elsevier Ltd. All rights reserved.

引用

页码：3062 / 3070

页数：9

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