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[reaction: see text] The synthesis of the C9-C26 portion of amphidinolide B1 is described. A Fleming allylation followed by elimination was employed for the construction of the C13-C15 diene portion. Sharpless asymmetric dihydroxylation was utilized for regioselective functionalization of a styrene-derived alkene, in the presence of the C13-C15 diene functionality. A highly diastereoselective aldol reaction was developed to establish the C18 stereochemistry.

Synthetic Studies toward Amphidinolide B1: Synthesis of the C9−C26 Fragment

Synthetic Studies toward Amphidinolide B₁: Synthesis of the C₉−C₂₆ Fragment