A simple procedure for the synthesis of γ-hydroxy-α,β-(E)-alkenoic esters: formal synthesis of (+)-macrosphelides A and B

A highly trans-selective conjugate reduction of γ-hydroxy-α,β-alkynoic esters to produce γ-hydroxy-α,β-(E)-alkenoic esters using LiAlH4 is reported. The application of this methodology is demonstrated by a formal synthesis of the potent cell–cell adhesion inhibitors (+)-macrosphelides A and B.