Studies in the synthesis of biaryl natural products: The 6,6′-binaphthopyranones

Michael J. Di Maso, Charles I. Grove, Jared T. Shaw

Research output: Chapter in Book/Report/Conference proceedingChapter

1 Scopus citations

Abstract

Efficient and enantioselective syntheses of a family of 6,6′-binaphthopyranone natural products (viriditoxin, pigmentosin A, talaroderxine A, and talaroderxine B) are reported. A vanadium-catalyzed oxidative coupling provides the key axial chirality in high diastereoselectivity. A unified Michael-Dieckman annulation strategy allows for access to the coupling precursors from an orthogonally protected orsellinate ester and the requisite α,β-unsaturated pyranones, which are synthesized through various enantioselective strategies. Herein, we report the successful syntheses of these natural products and their use in our continued efforts in studying the bacterial cell division protein, FtsZ.

Original languageEnglish (US)
Title of host publicationStrategies and Tactics in Organic Synthesis
PublisherAcademic Press Inc.
Pages225-248
Number of pages24
Volume10
ISBN (Print)9780124171855
DOIs
StatePublished - 2014

Publication series

NameStrategies and Tactics in Organic Synthesis
Volume10
ISSN (Print)18746004

Keywords

  • Axial chirality
  • Biaryl bond formation
  • Binaphthopyranone
  • FtsZ
  • Oxidative coupling
  • Pyranone
  • Vanadium catalysis

ASJC Scopus subject areas

  • Organic Chemistry
  • Drug Discovery

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    Di Maso, M. J., Grove, C. I., & Shaw, J. T. (2014). Studies in the synthesis of biaryl natural products: The 6,6′-binaphthopyranones. In Strategies and Tactics in Organic Synthesis (Vol. 10, pp. 225-248). (Strategies and Tactics in Organic Synthesis; Vol. 10). Academic Press Inc.. https://doi.org/10.1016/B978-0-12-417185-5.00010-7