Transannular rearrangement of activated 2,5-diketopiperazines: a key route to original scaffolds, - Archive ouverte HAL Accéder directement au contenu
Article Dans Une Revue Organic & Biomolecular Chemistry Année : 2008

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

Résumé

An efficient and original stereocontrolled transannular rearrangement starting from activated 2,5-diketopiperazines has been developed, an opportunity for the medicinal chemistry field, wich 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

Domaines

Chimie organique
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Dates et versions

hal-00359095 , version 1 (05-02-2009)

Identifiants

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Daniel Farran, Isabelle Parrot, Loic Toupet, Jean Martinez, Georges Dewynter. Transannular rearrangement of activated 2,5-diketopiperazines: a key route to original scaffolds,. Organic & Biomolecular Chemistry, 2008, 6, pp.3989-3996. ⟨10.139/b810352f⟩. ⟨hal-00359095⟩
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