Total synthesis of polygalolide a by intramolecular C-glycosylation

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Abstract

Total synyhesis of polygalolide A, a secondary metabolite isolated from a Chinese medicinal plant, was achieved. In order to construct an oxabicyclo [3.2.1] core skeleton, we have developed an intramolecular Ferrier-type C-glycosylation of a glucal modified with siloxyfuran as an internal nucleophile. Although the conditions found in the model experiments did not undergo the C-glycosylation, further examination led us to find that combination of TMSOTf and 2,4,6-collidine was the best condition, giving oxabicyclo [3.2.l]octene with correct quaternary stereogenic centers in high yield. The successful production of the single diastereomer indicated that the siloxy group at the C-3 position played a crucial role for the stereocontrol. After transformation into tetracyclic intermediate, a phenolic moiety was finally introduced by Mukaiyama aldol reaction to furnish polygalolide A.

Original languageEnglish
Pages (from-to)607-615
Number of pages9
JournalYuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry
Volume73
Issue number6
DOIs
Publication statusPublished - 2015 Jun
Externally publishedYes

Keywords

  • Asymmetric synthesis
  • C-glycosylation
  • Glucal
  • Natural products
  • Polygalolide
  • Siloxyfuran
  • Total synthesis

ASJC Scopus subject areas

  • Organic Chemistry

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