Total synthesis of papulacandin D

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

Research output: Contribution to journalArticlepeer-review


A total synthesis of the antifungal agent papulacandin D is reported. The molecule is representative of a large class of C-aryl glycosides that exhibit significant antifungal activity. The synthetic strategy bifurcates the molecule into two nearly equal subunits, the arylglycoside 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. The synthesis was accomplished in 31 steps overall from commercial starting materials to afford over 50 mg of the natural product.

Original languageEnglish (US)
Pages (from-to)2774-2776
Number of pages3
JournalJournal of the American Chemical Society
Issue number10
StatePublished - Mar 14 2007

ASJC Scopus subject areas

  • Catalysis
  • General Chemistry
  • Biochemistry
  • Colloid and Surface Chemistry


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