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

Authors

  • Pascal Hayoz
  • Anton Aeby
  • Cecile Pasquier
  • Reinhard Neier

DOI:

https://doi.org/10.2533/chimia.1993.230

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.

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Published

1993-06-30

Issue

Vol. 47 No. 6 (1993): La Chimie à Neuchâtel

Section

Forschung

License

Copyright (c) 1993 Swiss Chemical Society

Creative Commons License

This work is licensed under a Creative Commons Attribution-NonCommercial 4.0 International License.

How to Cite

[1]
P. Hayoz, A. Aeby, C. Pasquier, R. Neier, Chimia 1993, 47, 230, DOI: 10.2533/chimia.1993.230.