Faculté des sciences

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

Hayoz, Pascal ; Aeby, Anton ; Neier, Reinhard

In: Chimia, 1993, vol. 47, p. 230-232

A novel six-step synthesis of rac-5-(hydroxymethyl)-l-(tetrahydro-2'-oxo-fur-3'-yl)-lH-pyrrole-2-carboxaldehyde (rac-1) starting from 2-methylfuran has been developed. The key step is the formation of rac-2-methyl-l-(tetrahydro-2'-oxofur-3'-yl)- lH-pyrrole (rac-7) according to the Clauson-Kaas procedure. Subsequent Vilsmeier... Plus

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