Synthesis of (+)-discodermolide and analogues by control of asymmetric induction in aldol reactions of γ-chiral (Z)-enals

The boron-mediated aldol reactions of the (Z)-enals 3 and 7 proceed with high levels of 1,4-stereoinduction arising from the γ-substituent. Reagent control from (+)-Ipc2BCl can be used effectively to overturn this substrate bias, thus enabling the stereocontrolled formation of (+)-discodermolide (1) and related analogues 15–18.