CHIMIA (Jun 1993)

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

  • Pascal Hayoz,
  • Anton Aeby,
  • Cecile Pasquier,
  • Reinhard Neier

Journal volume & issue
Vol. 47, no. 6

Abstract

Read online

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.