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

Organic & Biomolecular Chemistry
Youngeun Jung, Ikyon Kim

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.

References

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Jan 7, 2015·The Journal of Organic Chemistry·Youngeun Jung, Ikyon Kim

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Citations

Feb 2, 2017·Beilstein Journal of Organic Chemistry·Dimpee GogoiSajal Kumar Das
Oct 23, 2019·The Journal of Organic Chemistry·Vanessa ArredondoDavid L Van Vranken

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