An Efficient Enantioselective Synthesis of the 3C Protease Inhibitor (-)-Thysanone

Sperry, Jonathan; Brimble, Margaret

An Efficient Enantioselective Synthesis of the 3C Protease Inhibitor (-)-Thysanone

Sperry, Jonathan

Brimble, Margaret

Reference

Synlett 2008(12):1910-1912 2008

Abstract

The enantioselective synthesis of the 3C protease inhibitor (-)-thysanone is described. The key step is the o-toluate anion addition to an α,β-unsaturated δ-lactone. Spectroscopic analysis of the synthetic material confirms the 1R,3S stereochemistry of the natural product.

DOI

10.1055/s-2008-1078590

Keywords

thysanone, pyranonaphthoquinone, 3C protease, 3C-PROTEASE INHIBITOR, PYRANONAPHTHOQUINONE ANTIBIOTICS, ABSOLUTE-CONFIGURATION, BIOLOGICAL-ACTIVITY, HAUSER ANNULATION, DEOXY ANALOGS, THYSANONE, STEREOCHEMISTRY