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Harnessing Quinone Methides: Total Synthesis of (±)‐Vaticanol A
Author(s) -
Jepsen Tue H.,
Thomas Stephen B.,
Lin Yunqing,
Stathakis Christos I.,
de Miguel Irene,
Snyder Scott A.
Publication year - 2014
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201402858
Subject(s) - quinone , trimer , diastereomer , quinone methide , chemistry , total synthesis , resveratrol , polyphenol , sequence (biology) , stereochemistry , combinatorial chemistry , organic chemistry , dimer , biochemistry , antioxidant
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.