Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 53, Issue 26, Pages 6747-6751Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201402858
Keywords
Friedel-Crafts reaction; natural products; quinone methide; resveratrol; total synthesis
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Funding
- National Institutes of Health [R01-GM84994]
- Bristol-Myers Squibb
- Eli Lilly
- Amgen
- NSF
- Research Corporation for Science Advancement
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Although quinone methides are often postulated as intermediates in the biosynthesis of many polyphenolic natural products, deploying their power in a laboratory setting to achieve similar bond constructions has sometimes proven challenging. Herein, a total synthesis of the resveratrol trimer vaticanol A has been achieved through three instances of quinone methide chemistry. These operations, one of which succeeded only under very specific conditions, expediently generated its [7,5]-carbocyclic core, afforded a unique sequence for dihydrobenzofuran formation, and concurrently generated, in addition to the target molecule, a series of diastereomers reflective of many other isolates.
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