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

Author

Horst Antonicek, Jürgen Scherkenbeck, W.R. Christian Beyer, Bettina Lüke, Michael Schindler, and Katharina Woithe

Subjects
SERCA, Thapsigargin, biology, Indole alkaloid, Stereochemistry, ATPase, Organic Chemistry, Total synthesis, Biochemistry, Terpenoid, chemistry.chemical_compound, chemistry, Drug Discovery, biology.protein, Cyclopiazonic acid
Abstract

The indole alkaloid α-cyclopiazonic acid (CPA) is one of the few known inhibitors of sarco( endo )plasmic reticulum Ca 2+ -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.

Published
2011
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