Total synthesis of cis-solamin A, a mono-tetrahydrofuran acetogenin isolated from Annona muricata

Total synthesis of cis-solamin A was accomplished without using protecting groups starting from (−)-muricatacin in 11 steps with an overall yield of 4.5%. The backbone of cis-solamin A was constructed by olefin cross-metathesis between the tetrahydrofuran moiety and γ-lactone moiety. An enzymatic kinetic transesterification procedure was successfully applied to the synthesis of an optically pure γ-lactone moiety.