Efficient access to the core of the Strychnos, Aspidosperma and Iboga alkaloids. A short synthesis of norfluorocurarine

David B C Martin; Christopher D Vanderwal

doi:10.1021/ja900640v

Efficient access to the core of the Strychnos, Aspidosperma and Iboga alkaloids. A short synthesis of norfluorocurarine

J Am Chem Soc. 2009 Mar 18;131(10):3472-3. doi: 10.1021/ja900640v.

Authors

David B C Martin¹, Christopher D Vanderwal

Affiliation

¹ Department of Chemistry, The University of California, Irvine, California 92697-2025, USA.

PMID: 19236094
DOI: 10.1021/ja900640v

Abstract

An efficient anionic bicyclization of tryptamine-derived Zincke aldehydes forms the basis for a three-step route to the tetracyclic ABCE core of many Strychnos, Aspidosperma, and Iboga alkaloids. This powerful reaction is showcased in a five-step synthesis of the Strychnos alkaloid norfluorocurarine from tryptamine and pyridine.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Alkaloids / chemistry*
Aspidosperma / chemistry*
Crystallography, X-Ray
Strychnos / chemistry*
Tabernaemontana / chemistry*
Tubocurarine / analogs & derivatives*
Tubocurarine / chemical synthesis

Substances

Alkaloids
norfluorocurarine
Tubocurarine