Stereochemical revision of communiols D and H through synthesis

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11 Citations (Scopus)

Abstract

Based on the previously revised stereochemistries for communiols A-C, the ent-8-epi- and ent-6-epi-stereoisomers of the original structures proposed for communiols D and H, respectively, were synthesized as highly probable candidates for their genuine structures by using the Sharpless asymmetric dihydroxylation as the source of chirality. Complete accord in spectral properties between each synthetic candidate and the corresponding natural material as well as the fact that communiols A-D and H were all isolated from the same fungal source, led us to the conclusion that the stereochemistries of communiols D and H should also be revised to their (3S,5S,7R,8S,11R)- and (5S,7R,8S)-forms, respectively.

Original languageEnglish
Pages (from-to)1102-1109
Number of pages8
JournalTetrahedron
Volume62
Issue number6
DOIs
Publication statusPublished - 2006 Feb 6

Keywords

  • Asymmetric dihydroxylation
  • Communiol
  • Dioxabicyclo[3.3.0]octane
  • Enantioselective synthesis
  • Podospora communis

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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