Studies directed toward the total synthesis of 14-membered cyclopeptide alkaloids: Synthesis of a cyclic precursor to nummularine-F

Article abstract of DOI:10.1016/S0040-4039(01)93413-6

A highly strained 14-membered para-ansa cyclopeptide, a potential precursor of the cyclopeptide alkaloid, nummularine-F, was made by cyclization of a pentafluorophenyl ester under catalytic hydrogenation conditions. This cyclization and the stereoselective synthesis of the acyclic activated ester from D-serine, are presented.