Philippe Pitchen

Large scale asymmetric synthesis of a biologically active sulfoxide

Abstract The asymmetric synthesis of sulfoxide RP 73163 is described. The synthetic strategy is based on the enantioselective oxidation of a suitably designed prochiral methyl sulfide, followed by α alkylation of the resulting sulfoxide.

Bis-deoxygenation of methyl 3,6-anhydro-D-pyranosides

Abstract The synthesis and radical reduction of thiocarbonyl derivatives of methyl 3,6-anhydro pyranosides has been studied in the α-D-gluco, α-D-manno and β-D-galacto series. A cyclic intermediate is proposed to explain the fact that bis-deoxygenation only occurred in the galactose series, providing a 3 step synthesis of the desired product 1b .