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Issue 25, 2005

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

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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

Supplementary files

Article information


Submitted
19 Nov 2004
Accepted
27 Jan 2005
First published
18 May 2005

Chem. Commun., 2005, 3162-3164
Article type
Communication

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

C. M. Haskins and D. W. Knight, Chem. Commun., 2005, 3162 DOI: 10.1039/B417625C

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