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Letters in Organic Chemistry

Author(s): Chithaluri Sudhakar*, Kottolla Sai Prasad and Batharaju Ramesh

DOI: 10.2174/1570178620666230522115248

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

Page: [1010 - 1015] Pages: 6

  • * (Excluding Mailing and Handling)

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.

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