Diastereoselective Aldol Reactions of β-Silyloxy Ethyl Ketones. Application to the Total Synthesis of Bafilomycin A1

Article abstract of DOI:10.1016/S0040-4039(00)91817-3

Studies directed toward the C₁₇-C₁₈ aldol bond construction in the macrolide antibiotic bafilomycin A₁ are described.The effect of the β-substituent in the aldol reactions of α-unsubstituted enolates is documented for various model compounds.The stereoselectivity of this process is critically dependent on the C₂₁ and C₂₃ oxygen protecting groups.Application of this methodology to the synthesis of bafilomycin A₁ is reported.