Total synthesis of Michellamines A-C: Important anti-HIV agents

Thomas R. Hoye, Minzhang Chen, Liang Mi, Owen P. Priest

Research output: Contribution to journalArticlepeer-review

64 Scopus citations

Abstract

Michellamines A-C have been prepared by total synthesis in 7 and 16 linear steps from known and commercial materials, respectively. Key steps include i) palladium(0)-mediated biaryl coupling, ii) silver oxide promoted oxidative 1-naphthol coupling to an atropisomeric mixture of cross-ring quinones (indigoids), and iii) simultaneous per-debenzylation/reductive bleaching to the central 2,2′-binaphthol.

Original languageEnglish (US)
Pages (from-to)8747-8750
Number of pages4
JournalTetrahedron Letters
Volume35
Issue number47
DOIs
StatePublished - Nov 21 1994

Bibliographical note

Funding Information:
Acknowledgments This work was supported by grant #CA-M284 awarded by the DHHS. A sample of natural michellamine B was kindly provided by Dr. Ven L. Narayanan of the Drug Synthesis & Chemistry Branch, Developmental Therapeutics Program, Division of Cancer Treatment, National Cancer Institute.

Copyright:
Copyright 2014 Elsevier B.V., All rights reserved.

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