The stereoselective syntheses of 2-cyclopropyl and (2S)-2-hydroxymethyl-(3R,4S)-4-hydroxy-beta3-homoproline are described. The reported amino acids were constructed through 1,3-dipolar cycloaddition of strained alkylidenecyclopropanes with enantiopure pyrroline N-oxides derived from malic acid followed by thermal rearrangement of the adducts in the presence of trifluoroacetic acid. The two-step sequence afforded the homoprolines suitably protected to be directly used as building blocks in peptidomimetic synthesis as proved by the synthesis of the two model mixed alpha/beta/alpha tripeptides Phe-beta3-HPro-Val
Synthesis of 4-hydroxy-β3-homoprolines and their insertion in α/β/α-tripeptides / F. M. Cordero; C. Vurchio; M. Lumini; A. Brandi. - In: AMINO ACIDS. - ISSN 0939-4451. - STAMPA. - (2013), pp. 769-780. [10.1007/s00726-012-1401-0]
Synthesis of 4-hydroxy-β3-homoprolines and their insertion in α/β/α-tripeptides
CORDERO, FRANCA MARIA;VURCHIO, CAROLINA;BRANDI, ALBERTO
2013
Abstract
The stereoselective syntheses of 2-cyclopropyl and (2S)-2-hydroxymethyl-(3R,4S)-4-hydroxy-beta3-homoproline are described. The reported amino acids were constructed through 1,3-dipolar cycloaddition of strained alkylidenecyclopropanes with enantiopure pyrroline N-oxides derived from malic acid followed by thermal rearrangement of the adducts in the presence of trifluoroacetic acid. The two-step sequence afforded the homoprolines suitably protected to be directly used as building blocks in peptidomimetic synthesis as proved by the synthesis of the two model mixed alpha/beta/alpha tripeptides Phe-beta3-HPro-ValFile | Dimensione | Formato | |
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