A Novel Synthesis of rac-5-(Hydroxymethyl)-1-(Tetrahydro-2'-oxofur-3'-yl)-1H-pyrrole-2-carboxaldehyde

Abstract

A novel six-step synthesis of rac-5-(hydroxymethyl)-1-(tetrahydro-2'-oxo-fur-3'-yl)-1H-pyrrole-2-carboxaldehyde (rac-1) starting from 2-methylfuran has been developed. The key step is the formation of rac-2-methyl-1-(tetrahydro-2'-oxofur-3'- yl)-1H-pyrrole (rac-7) according to the Clauson-Kaas procedure. Subsequent Vilsmeier formylation, oxidation with lead tetraacetate, and enzymatic hydrolysis led to rac-1.