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 language | English (US) |
|---|---|
| Pages (from-to) | 8747-8750 |
| Number of pages | 4 |
| Journal | Tetrahedron Letters |
| Volume | 35 |
| Issue number | 47 |
| DOIs | |
| State | Published - 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.
