Total Synthesis of Xestodecalactone C via Sharpless Epoxidation and Friedal-Crafts Acylation

Abstract

Abstract: Marine-derived macrolides that occur naturally exhibit a range of biological properties, including antibacterial and antifungal activity. : Sharpless epoxidation and intramolecular acylation via the Friedel-Crafts method for the macrolide ring formation was used as the main steps in the regioselective construction of naturally existing xestodecalactone C, which was started from chiral propylene oxide. : The isolated yellow coloured final product had a 91% yield, and FT-IR, Mass, 1H-NMR, and 13C NMR were used to characterise each product. As a result, chiral propylene oxide was used as the starting material for the regioselective total synthesis of the naturally occurring xestrodecalactone C, with the main stages being intramolecular Friedel-Crafts acylation for macrolide ring formation and Sharpless epoxidation. The synthesis of numerous xestrodecalactone C analogues relevant for bioevaluation can be done quickly and easily using this synthetic approach.