Harnessing Quinone Methides: Total Synthesis of (±)‐Vaticanol A |
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Authors: | Tue H Jepsen Stephen B Thomas Yunqing Lin Dr Christos I Stathakis Irene de?Miguel Prof?Dr Scott A Snyder |
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Institution: | 1. Dept. of Chemistry, Columbia University, 3000 Broadway, New York, NY 10027 (USA);2. Dept. of Chemistry, The Scripps Research Institute, 130 Scripps Way, Jupiter, FL 33458 (USA) http://www.scripps.edu/snyder/index.htm |
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Abstract: | 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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Keywords: | Friedel– Crafts reaction natural products quinone methide resveratrol total synthesis |
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