Practical stereoselective synthesis of conformationally constrained unnatural proline-based amino acids and peptidomimetics
2001; Elsevier BV; Volume: 57; Issue: 30 Linguagem: Inglês
10.1016/s0040-4020(01)00538-5
ISSN1464-5416
AutoresLaura Belvisi, Lino Colombo, Matteo Colombo, Marcello Di Giacomo, Leonardo Manzoni, Bruno Vodopivec, Carlo Scolastico,
Tópico(s)Synthesis and Catalytic Reactions
ResumoA practical synthetic scheme was developed to prepare both the cis- and trans-fused stereoisomers of N-Boc-l-octahydroindole-2-carboxylic acid (l-Oic) methyl ester. Key event of the synthetic sequence was the ring-closing metathesis of a suitable diallylated proline derivative. This is the first reported practical synthesis of the trans-fused isomer. Functionalization of the octahydroindole nucleus by electrochemical oxidation followed by acid-catalysed allylation paved the way for the preparation of reverse-turn dipeptide mimics.
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