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

Youngeun Jung, Ikyon Kim

Research output: Contribution to journalArticle

7 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

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acetates
Acetates
acetylation
Acetylation
acids
Acids
Cyclization
Palladium
Ether
installing
palladium
ethers
routes
Molecules
molecules
brazilin

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

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A concise synthetic approach to brazilin via Pd-catalyzed allylic arylation. / Jung, Youngeun; Kim, Ikyon.

In: Organic and Biomolecular Chemistry, Vol. 13, No. 14, 14.04.2015, p. 4331-4335.

Research output: Contribution to journalArticle

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