Synthesis of C9-C13 and C15-C21 Subunits of Discodermolide

A new synthetic strategy for the construction of two polypropionate subunits of discodermolide, a highly potent anticancer natural product, is reported. The strategy relies on two key reactions: a Shimizu non-aldol reaction, a stereoselective hydrogenolysis of alkenyl epoxides, to generate thesynhydroxy-methyl moiety and a NaBH4-BF3.OEt(2)mediated hydride addition reaction. By utilizing this strategy, two different fragments of discodermolide, C9-C13 subunit and C15-C21 subunit have been successfully synthesized.