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

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Journal article

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

David B C Martin and Christopher D Vanderwal

Journal of the American Chemical Society, Vol.131(10), pp.3472-3473

03/18/2009

DOI: 10.1021/ja900640v

PMID: 19236094

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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.

Tubocurarine - analogs & derivatives

Tubocurarine - chemical synthesis

Tabernaemontana - chemistry

Crystallography, X-Ray

Aspidosperma - chemistry

Strychnos - chemistry

Alkaloids - chemistry

Details

Title: Subtitle: Efficient access to the core of the Strychnos, Aspidosperma and Iboga alkaloids. A short synthesis of norfluorocurarine
Creators: David B C Martin - Department of Chemistry, The University of California, Irvine, California 92697-2025, USA
Christopher D Vanderwal
Resource Type: Journal article
Publication Details: Journal of the American Chemical Society, Vol.131(10), pp.3472-3473
Publisher: United States
DOI: 10.1021/ja900640v
PMID: 19236094
ISSN: 0002-7863
eISSN: 1520-5126
Language: English
Date published: 03/18/2009
Academic Unit: Iowa Neuroscience Institute; Chemistry
Record Identifier: 9984065856802771

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