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Article

Total Synthesis of (±)-Aspidospermidine

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Matthew A. Toczko and Clayton H. Heathcock*

Department of Chemistry, University of California, Berkeley, California 94720

J. Org. Chem., 2000, 65 (9), pp 2642–2645

DOI: 10.1021/jo991599s

Publication Date (Web): April 13, 2000

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

Abstract

(±)-Aspidospermidine (1) has been synthesized from readily available methyl 3-ethyl-2-oxocylopentanecarboxylate (17) in 5.9% yield over 13 steps. The key step of the synthesis is an intramolecular cascade reaction that simultaneously forms the B, C, and D rings of 1. A high-yielding method of closing the remaining E ring is also described.

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Published In Issue May 05, 2000
Received October 13, 1999

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Article

Total Synthesis of (±)-Aspidospermidine

Abstract

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History

Recommend & Share

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