Synthesis of 6,6′-binaphthopyran-2-one natural products: Pigmentosin A, talaroderxines A and B

Charles I. Grove, Michael J. Di Maso, Firoz A. Jaipuri, Michelle B. Kim, Jared T. Shaw

Research output: Contribution to journalArticle

20 Scopus citations

Abstract

Efficient and stereoselective syntheses of pigmentosin A, talaroderxine A, and its diastereomer talaroderxine B are reported. The binaphthyl ring system is assembled by vanadium-catalyzed phenolic coupling of tricyclic precursors. These key intermediates were prepared by Michael-Dieckmann annulation of a protected orsellinate ester, with the requisite pyranones accessed by a new variant of Ghosez's sulfone-epoxide annulation. Preliminary biological experiments are reported for pigmentosin.

Original languageEnglish (US)
Pages (from-to)4338-4341
Number of pages4
JournalOrganic Letters
Volume14
Issue number17
DOIs
StatePublished - Sep 7 2012

ASJC Scopus subject areas

  • Organic Chemistry
  • Physical and Theoretical Chemistry
  • Biochemistry

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    Grove, C. I., Di Maso, M. J., Jaipuri, F. A., Kim, M. B., & Shaw, J. T. (2012). Synthesis of 6,6′-binaphthopyran-2-one natural products: Pigmentosin A, talaroderxines A and B. Organic Letters, 14(17), 4338-4341. https://doi.org/10.1021/ol301743t