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

oleh: Pascal Hayoz, Anton Aeby, Cecile Pasquier, Reinhard Neier

Format: Article
Diterbitkan: Swiss Chemical Society 1993-06-01

Deskripsi

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.