Open AccessA Novel Synthesis of rac-5-(Hydroxymethyl)-1-(Tetrahydro-2'-oxofur-3'-yl)-1H-pyrrole-2-carboxaldehyde
Author(s) -
Pascal Hayoz,
Anton Aeby,
Cecile Pasquier,
Reinhard Neier
Publication year - 1993
Publication title -
chimia
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.387
H-Index - 55
eISSN - 2673-2424
pISSN - 0009-4293
DOI - 10.2533/chimia.1993.230
Subject(s) - formylation , pyrrole , hydroxymethyl , chemistry , combinatorial chemistry , hydrolysis , stereochemistry , organic chemistry , catalysis
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.