S. Denmark, Christopher S. Regens, Tetsuya Kobayashi
Mar 1, 2007
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2
Influential Citations
102
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Journal
Journal of the American Chemical Society
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.