A Novel Synthesis of rac-5-(Hydroxymethyl)-l-Tetrahydro-21-oxofur-31-yl)-1H-pyrrole-2-carboxaldehyde

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