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

Organic & Biomolecular Chemistry Pub Date: 2015-02-11 DOI: 10.1039/C5OB00023H

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.

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