Harnessing quinone methides: total synthesis of (±)-vaticanol A.
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.
Dept. of Chemistry, Columbia University, 3000 Broadway, New York, NY 10027 (USA).
Tue H
TH
Jepsen
Stephen B
SB
Thomas
Yunqing
Y
Lin
Christos I
CI
Stathakis
Irene
I
de Miguel
Scott A
SA
Snyder
D001688:Biological Products / Q000138:chemical synthesis / Q000737:chemistry; D045563:Indolequinones / Q000737:chemistry*; D000077185:Resveratrol; D013237:Stereoisomerism; D013267:Stilbenes / Q000138:chemical synthesis* / Q000737:chemistry
D001688:Biological Products; D045563:Indolequinones; D013267:Stilbenes; C000597354:vaticanol A; C068040:quinone methide; D000077185:Resveratrol
Friedel-Crafts reaction; natural products; quinone methide; resveratrol; total synthesis