Total synthesis of brazilin

Youngeun Jung, Ikyon Kim

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28 Citations (Scopus)

Abstract

Described herein is a highly efficient total synthesis of brazilin from commercially available starting materials in 9 steps with 70% overall yield. Mitsunobu coupling followed by In(III)-catalyzed alkyne-aldehyde metathesis allowed for rapid construction of brazilin core skeleton in quantitative yield. Subsequent modulation of oxidation levels and acid-catalyzed cyclization led to the trimethyl ether of brazilin. Asymmetric dihydroxylation of the key intermediate was also demonstrated, which would permit asymmetric access to (+)-brazilin.

Original languageEnglish
Pages (from-to)2001-2005
Number of pages5
JournalJournal of Organic Chemistry
Volume80
Issue number3
DOIs
Publication statusPublished - 2015 Feb 6

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All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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