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We are grateful to the National Institutes of Health (GM-50151) for generous financial support. We thank Prof. D. Stierle for copies of spectral data of berkelic acid and berkelic acid methyl ester and Artem Shvartsbart for experimental assistance.
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Communication
Synthesis of (−)-Berkelic Acid†
Article first published online: 12 JAN 2009
DOI: 10.1002/anie.200805488
Copyright © 2009 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Additional Information
How to Cite
Wu, X., Zhou, J. and Snider, Barry B. (2009), Synthesis of (−)-Berkelic Acid. Angew. Chem. Int. Ed., 48: 1283–1286. doi: 10.1002/anie.200805488
- †
Publication History
- Issue published online: 28 JAN 2009
- Article first published online: 12 JAN 2009
- Manuscript Received: 11 NOV 2008
Funded by
- National Institutes of Health. Grant Number: GM-50151
Keywords:
- antitumor agents;
- heterocycles;
- spiroketals;
- structure elucidation
Abstract
An extremophilic challenge: Stereospecific condensation of a fully functionalized ketal aldehyde and a 2,6-dihydroxybenzoic acid is the key step in the synthesis of (−)-berkelic acid confirming Fürstner's reassignment of the stereochemistry at C18 and C19, establishing the absolute stereochemistry, and tentatively assigning the stereochemistry at C22.