Synthesis of (+)-Patulolide C Using R-(+)-γ-Valerolactone as a Chiral Synthon.

摘要

The total synthesis of (+)-Patulolide-C is accomplished by using enantiopure R-(+)-γ-valerolactone & R-(+)-epichlorohydrin as chiral synthons. The strategy adopted for the synthesis is a convergent approach wherein two advanced intermediates were synthesized independently using the chiral synthons and coupled to achieve the skeleton of Patulolide-C. The important synthetic steps of the synthesis are two carbon homologation of the cyclic lactol, Julia olefination of enone with sulfone in DME, DIBAl-H mediated regioselective opening of benzylidine acetal, selective oxidation of primary alcohol to aldehyde using BAIB/TEMPO and lactonization of seco-acid adopting Yamaguchi protocol to afford the macrolide skeleton.