1,6-Asymmetric Induction in Boron-Mediated Aldol Reactions: Application to a Practical Total Synthesis of (+)-Discodermolide

摘要

By relying solely on substrate-based stereocontrol, a practical total synthesis of the microtubule-stabilizing anticancer agent (+)-discodermolide has been realized. This exploits a novel aldol bond construction with 1,6-stereoinduction from the boron enolate of (Z)-enone 3 in addition to aldehyde 2. The 1,3-diol 7 is employed as a common building block for the C_1-c_5, C_9-C_(16), and C_(17)-C(24) subunits.