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A concise synthetic approach to brazilin via Pd-catalyzed allylic arylation†
Youngeun Jung,Ikyon Kim
Organic & Biomolecular Chemistry Pub Date : 03/03/2015 00:00:00 , DOI:10.1039/C5OB00216H
Abstract

A short synthetic route to the trimethyl ether of brazilin was developed in 6 steps from 7-methoxychromene with 78% overall yield. Regioselective installation of a formyl group onto 7-methoxychromene followed by reduction and acetylation afforded allylic acetate. Palladium-catalyzed allylic coupling of allylic acetate with arylboronic acid provided direct access to 3-benzylchromene which was converted to the target molecule upon ensuing dihydroxylation and acid-catalyzed cyclization in a highly concise manner.

Graphical abstract: A concise synthetic approach to brazilin via Pd-catalyzed allylic arylation
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