Synthetic studies on gambieric acids, potent antifungal polycyclic ether natural products: Reassignment of the absolute configuration of the nonacyclic polyether core by NMR analysis of model compounds

Haruhiko Fuwa, Kazuya Ishigai, Tomomi Goto, Akihiro Suzuki, Makoto Sasaki

Research output: Contribution to journalArticlepeer-review

23 Citations (Scopus)

Abstract

(Chemical Equation Presented) A highly stereocontrolled, convergent synthesis of the A/B-ring fragment of gambieric acids (GAs) has been developed on the basis of (i) a Suzuki-Miyaura coupling of the C1-C6 alkylborate and the C7-C17 vinyl iodide and (ii) a diastereoselective haloetherification for the construction of the A-ring tetrahydrofuran as key steps. Inspection of the 1H and 13C NMR chemical shifts of the synthesized A/B-ring model compounds led to a stereochemical reassignment of the absolute configuration of the polycyclic ether core of GAs. This structure revision was further supported by a synthesis of the A/BC-ring model compound of gambieric acid B and a comparison of its 1H and 13C NMR data with those of the natural product.

Original languageEnglish
Pages (from-to)4024-4040
Number of pages17
JournalJournal of Organic Chemistry
Volume74
Issue number11
DOIs
Publication statusPublished - 2009 Jun 5

ASJC Scopus subject areas

  • Organic Chemistry

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