Transannular rearrangement of activated 2,5-diketopiperazines: a key route to original scaffolds
Organic & Biomolecular Chemistry2008Vol. 6(21), pp. 3989–3989
Citations Over TimeTop 16% of 2008 papers
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.
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