Harnessing Quinone Methides: Total Synthesis of (±)‐Vaticanol A1. (19th May 2014)

• Record Type: Journal Article
• Authors: Jepsen, Tue H.; Thomas, Stephen B.; Lin, Yunqing; Stathakis, Christos I.; de Miguel, Irene; Snyder, Scott A.
• Is Part Of: Angewandte Chemie. Volume 126:Number 26(2014)
• Page Start: 6865
• Page End: 6869
• Publication Date: 2014-05-19
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1002/ange.201402858
• Languages: English
• ISSNs: 0044-8249

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>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.</p> </abstract>