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

P Hayoz, A Aeby, C Pasquier…

Index: Hayoz, Pascal; Aeby, Anton; Pasquier, Cecile; Neier, Reinhard Chimia, 1993 , vol. 47, # 6 p. 230 - 232

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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.