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Article

A Biomimetic Approach to the Discorhabdin Alkaloids: Total Syntheses of Discorhabdins C and E and Dethiadiscorhabdin D

Kelly Marshall Aubart and Clayton H. Heathcock*

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

J. Org. Chem., 1999, 64 (1), pp 16–22

DOI: 10.1021/jo9815397

Publication Date (Web): December 11, 1998

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

The characteristic spirodienone structure of the discorhabdin alkaloids is readily formed by reaction of the tyramine-substituted indoloquinonimines 26, 35, and 36 with cupric chloride, triethylamine, and oxygen. This cyclization provides a possibly biomimetic route to discorhabdins C and E (41 and 42). The unbrominated spirodienone 40 reacts with hydrogen over Pd/C to give enone 46. Bromination at the α position gives a mixture of bromoenones that undergo smooth conversion to dethiadiscorhabdin D (4) upon treatment with basic alumina.

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Published In Issue January 08, 1999
Received July 31, 1998

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Article

A Biomimetic Approach to the Discorhabdin Alkaloids: Total Syntheses of Discorhabdins C and E and Dethiadiscorhabdin D

Abstract

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Recommend & Share

Related Content

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A Concise Total Synthesis of (−)-Quinocarcin via Aryne Annulation

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