Synthetic studies directed towards epothilone A: enantioselective synthesis of a C7-C15 carboxaldehyde segment

Article abstract of DOI:10.1016/S0040-4039(97)10527-5

Enantioselective syntheses of a protected C₇-C₁₅ fragment of epothilone A is reported in ten manipulations in good overall yield. An alkynyl-aluminium induced opening of a chiral epoxide followed by recording of functionally furnished the iodide 18. Chain elongation with N-propionyl-1S-(-)-2,10-camphorsultam 19 afforded the elaborated acylsultam 20 which was reduced and reoxidized to furnish a protected chiral aldehyde 6 suitable for aldol condensation, representing the C₇-C₁₅ portion of epothilone A.