Transannular rearrangement of activated 2,5-diketopiperazines: a key route to original scaffolds |
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Authors: | Farran Daniel Parrot Isabelle Toupet Loïc Martinez Jean Dewynter Georges |
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Affiliation: | Institut des Biomolécules Max Mousseron, UMR CNRS 5247, Université Montpellier 1, Université Montpellier 2, Place Eugène Bataillon, 34095 Montpellier Cedex 5, France. |
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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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