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We are grateful to the NIH CA-109164 for financial support and to Eli Lilly (E.M.O.), Novartis (B.J.M.), and the American Chemical Society, Division of Organic Chemistry sponsored by Organic Syntheses (B.J.M.) for graduate fellowships. Special thanks go to Quest Pharmaceuticals for providing a sample of hypocrellin.
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Communication
Dynamic Stereochemistry Transfer in a Transannular Aldol Reaction: Total Synthesis of Hypocrellin A†
Article first published online: 27 MAY 2008
DOI: 10.1002/anie.200800734
Copyright © 2008 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Additional Information
How to Cite
O'Brien, Erin M., Morgan, Barbara J. and Kozlowski, Marisa C. (2008), Dynamic Stereochemistry Transfer in a Transannular Aldol Reaction: Total Synthesis of Hypocrellin A. Angew. Chem. Int. Ed., 47: 6877–6880. doi: 10.1002/anie.200800734
- †
Publication History
- Issue published online: 20 AUG 2008
- Article first published online: 27 MAY 2008
- Manuscript Received: 13 FEB 2008
Funded by
- NIH. Grant Number: CA-109164
- Eli Lilly
- Novartis
- American Chemical Society, Division of Organic Chemistry
- Quest Pharmaceuticals
Keywords:
- biaryls;
- cyclization;
- dynamic stereochemical transfer;
- natural products;
- total synthesis
A dynamic approach: The key step in the total synthesis of hypocrellin A involves a potentially biomimetic 1,8-diketone aldol reaction, which constructs the seven-membered ring. The helical configuration is established first from an axially chiral biaryl unit and is then used in a dynamic stereochemical transfer process to form the remaining stereocenters in the intramolecular aldol reaction (see scheme).