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

Youngeun Jung, Ikyon Kim

Research output: Contribution to journalArticle

9 Citations (Scopus)

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. This journal is

Original languageEnglish
Pages (from-to)4331-4335
Number of pages5
JournalOrganic and Biomolecular Chemistry
Volume13
Issue number14
DOIs
Publication statusPublished - 2015 Apr 14

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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