Enantioselective synthesis of the C1-C9 segment of bryostatin by kinetic resolution of racemic β-keto esters

Article abstract of DOI:10.1016/0040-4039(96)00172-4

The enantioselective synthesis of the C1-C9 segment of bryostatins is described. Racemic β-keto ester 2 was subjected to kinetic resolution. Reduction with baker's yeast establishes two of the three chiral centers. Chemical transformation of the terminal acetylene moiety generates aldehyde 5 which is transformed diastereoselectively to the corresponding alcohol 6 via Sakurai reaction.