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Synthesis of biomimetic precursors of isovelleral analogues.

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Author

Summary, in 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.

Publishing year

2008

Language

English

Pages

91-99

Publication/Series

Arkivoc

Volume

6

Document type

Journal article

Publisher

Arkat USA Inc

Topic

  • Organic Chemistry

Keywords

  • Biomimetic
  • isovelleral analogues
  • cytotoxic dialdehyde
  • methyl acetal

Status

Published

ISBN/ISSN/Other

  • ISSN: 1551-7012