Transannular rearrangement of activated 2,5-diketopiperazines: a key route to original scaffolds?

Organic & Biomolecular Chemistry Pub Date: 2008-09-03 DOI: 10.1039/B810352F

Abstract

An efficient and original stereocontrolled transannular rearrangement starting from activated 2,5-diketopiperazines has been developed, an opportunity for the medicinal chemistry field, which requests access to novel biological scaffolds. This powerful ring contraction, which can be related to a stereoselective aza-version of the Chan rearrangement, allows for example the one-step synthesis of various tetramic acids, access to 2-disubstituted statins, or the synthesis of relevant lactam-constrained dipeptide mimetics using a TRAL–RCM sequence.

Graphical abstract: Transannular rearrangement of activated 2,5-diketopiperazines: a key route to original scaffolds
Recommended Literature