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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 |
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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.