Synthetic Studies on a Pachastrissamine Sulfur Analogue: Synthesis of a 4-epi-Sulfur Analogue

Abstract

A versatile synthetic procedure for a sulfur analogue of pachastrissamine (jaspine B), which involves the tandem thiolation–cyclization of a 1,4-ditosylate to construct a tetrahydrothiophene ring, was developed. Nucleophilic amino substitution of a tetrahydrothiophene-4-sulfonate with unexpected retention of the configuration afforded the sulfur analogue of 4-epi-pachastrissamine.

Graphical Abstract