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Updated: May 17, 2026

Solid Phase Synthesis of a Functionalized Bis-Peptide Using "Safety Catch" Methodology
Published on: May 15, 2012
Synthesis of 4-hydroxy-β3-homoprolines and their insertion in α/β/α-tripeptides
Franca M Cordero1, Carolina Vurchio, Marco Lumini
1Dipartimento di Chimica Ugo Schiff, Università degli Studi di Firenze, Via della Lastruccia 13, 50019 Sesto Fiorentino, FI, Italy. franca.cordero@unifi.it
Abstract:
The stereoselective syntheses of 2-cyclopropyl- and (2S)-2-hydroxymethyl-(3R,4S)-4-hydroxy-β(3)-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 α/β/α tripeptides Phe-β(3)-HPro-Val.
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