Total synthesis of papulacandin D

Tetsuya Kobayashi, Christopher S. Regens, Scott E. Denmark

Research output: Contribution to journalArticlepeer-review

Abstract

A total synthesis of (+)-papulacandin D which shows an antifungal activity is reported. The molecule is one of the members of C-arylglycoside isolated from Papularia spherosperma. The synthetic strategy bifurcates the molecule into two nearly equal subunits, the aryl glycoside and 18-carbon fatty acid side chain. The key strategic transformations are (1) the palladium catalyzed, organosilanolate-based cross-coupling of a protected glucal silanol and (2) a catalytic enantioselective allylation of a dienal using allyltrichlorosilane. This highly convergent synthesis was accomplished in 31 steps overall from commercial starting materials.

Original languageEnglish (US)
Pages (from-to)616-628
Number of pages13
JournalYuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry
Volume66
Issue number6
DOIs
StatePublished - Jun 2008

Keywords

  • Asymmetric allylation
  • C-arylglycoside
  • Cross-metathesis
  • Enantioselective lewis base catalysis
  • Organo-silanol cross-coupling reac-tion
  • Palladium
  • Papulacandin
  • Total synthesis

ASJC Scopus subject areas

  • Organic Chemistry

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