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Aubart KM, Heathcock CH. A Biomimetic Approach to the Discorhabdin Alkaloids: Total Syntheses of Discorhabdins C and E and Dethiadiscorhabdin D. J Org Chem. 1999;64(1):16-22doi: 10.1021/jo9815397.
Aubart, K. M., & Heathcock, C. H. (1999). A Biomimetic Approach to the Discorhabdin Alkaloids: Total Syntheses of Discorhabdins C and E and Dethiadiscorhabdin D. The Journal of organic chemistry, 64(1), 16-22. https://doi.org/10.1021/jo9815397
Aubart, Kelly Marshall, and Heathcock, Clayton H.. "A Biomimetic Approach to the Discorhabdin Alkaloids: Total Syntheses of Discorhabdins C and E and Dethiadiscorhabdin D." The Journal of organic chemistry vol. 64,1 (1999): 16-22. doi: https://doi.org/10.1021/jo9815397
Aubart KM, Heathcock CH. A Biomimetic Approach to the Discorhabdin Alkaloids: Total Syntheses of Discorhabdins C and E and Dethiadiscorhabdin D. J Org Chem. 1999 Jan 08;64(1):16-22. doi: 10.1021/jo9815397. PMID: 11674079.
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J Org Chem. 1999 Jan 08;64(1):16-22. doi: 10.1021/jo9815397.

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

The Journal of organic chemistry

Kelly Marshall Aubart, Clayton H. Heathcock

Affiliations

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

PMID: 11674079 DOI: 10.1021/jo9815397

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 alpha position gives a mixture of bromoenones that undergo smooth conversion to dethiadiscorhabdin D (4) upon treatment with basic alumina.

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