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

Pascal Hayoz | Zendy; Anton Aeby | Zendy; Cecile Pasquier | Zendy; Reinhard Neier | Zendy

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A 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 international journal for chemistry

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.

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