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Synthesis of biomimetic precursors of isovelleral analogues.

Author:
  • Daniel Röme
  • Erwan Arzel
  • Martin H Johansson
  • Olov Sterner
Publishing year: 2008
Language: English
Pages: 91-99
Publication/Series: ARKIVOC
Volume: 6
Document type: Journal article
Publisher: Arkat USA Inc

Abstract english

Based on how the mushroom Lactarius vellereus converts an inactive precursor into the cytotoxic dialdehyde isovelleral (1) via a cyclic enol ether, as part of a binary chemical defense system that protects the fruit bodies against parasites, a synthetic way to obtain analogous dialdehydes masked in the same way has been developed. As isovelleral analogues (e.g. 2 and 3) possess extremely potent cytotoxic activity, but display low selectivity as their biological activity is linked to their reactivity, suitably masked isovelleraloids that are converted to the corresponding dialdehyde under specific conditions, may constitute a way to utilize these potent compounds. Specifically, compounds 4 and 5, biomimetic precursors of the isovelleral analogues 2 and 3, but trapped as the stable methyl acetals, have been prepared.

Keywords

  • Organic Chemistry
  • Biomimetic
  • isovelleral analogues
  • cytotoxic dialdehyde
  • methyl acetal

Other

Published
  • ISSN: 1424-6376
Olov Sterner
E-mail: olov [dot] sterner [at] science [dot] lu [dot] se

Dean

Faculty of Science

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Professor

Centre for Analysis and Synthesis

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