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. Copyright
Denmark, Scott E.,Regens, Christopher S.,Kobayashi, Tetsuya
p. 2774 - 2776
(2008/02/02)
More Articles about upstream products of 934243-71-7
Get Best Price for934243-71-71,5-anhydro-4,6-O-[bis(1,1-dimethylethyl)silylene]-1-C-[2',4'-bis(phenylmethoxy)-6'-(hydroxymethyl)phenyl]-2-deoxy-3-O-triethylsilyl-D-arabino-1-hexenitol