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

Abstract

AbstractThe 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.