A total synthesis of (±)-α-cyclopiazonic acid using a cationic cascade?

Chemical Communications Pub Date: 2005-05-18 DOI: 10.1039/B417625C

Abstract

The indolic terpene alkaloid α-cyclopiazonic acid 1 has been prepared in 11 steps from indole-4-methanol 6; the key step is a carbocationic cascade, terminated by a 4-nitrosulfonamide group and initiated by benzylic carbocation formation directly from the intermediate 9, which gives the tetracyclic product 10 in 74% yield.

Graphical abstract: A total synthesis of (±)-α-cyclopiazonic acid using a cationic cascade
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