A benzotriazole-mediated route to protected marine-derived hetero-2,5-diketopiperazines containing proline

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Abstract

A procedure for the cyclization of dipeptidoyl benzotriazolides containing proline derivatives promoted by triethylamine under MW activation is introduced. The reaction is general for a variety of dipeptidoyl benzotriazolides and represents a very practical and convenient method for the preparation of Pro- or Hyp-derived 2,5-diketopiperazines (2,5-DKPs) and bis-DKPs with a disulfide linker. This method can be used for the construction of 2,5-DKP compound libraries and for the synthesis of natural products with diketopiperazine cores.

Original languageEnglish (US)
Pages (from-to)4399-403
Number of pages5
JournalOrganic and Biomolecular Chemistry
Volume13
Issue number15
DOIs
StatePublished - Apr 21 2015

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Keywords

  • Animals
  • Biological Products
  • Cyclization
  • Diketopiperazines
  • Dipeptides
  • Ethylamines
  • Porifera
  • Proline
  • Stereoisomerism
  • Triazoles
  • Journal Article
  • Research Support, Non-U.S. Gov't

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