Studies towards total synthesis of borrelidin, stereoselective synthesis of the polysubstituted macrolidic part

Article abstract of DOI:10.1016/S0040-4039(97)01371-3

Enantioselective synthesis of the polysubstituted macrolidic part of borrelidin (1) is presented. Six out of the nine stereogenic centers in 12 and 13 were achieved in >99.2 %ee in seven steps from meso-diol 4. The synthesis is based on enantioselective formation of bis-epoxide 10 followed by regioselective alkylation of the epoxide functionalities.