Synthesis of Conformationally Restricted and Optically Pure Analogues of Serine-Proline Dipeptide via Aldol Condensation

Fabio Massimo Bravin; Gilberto Busnelli; Matteo Colombo; Francesco Gatti; Leonardo Manzoni; Carlo Scolastico

doi:10.1055/s-2004-815921

PAPER

Synthesis of Conformationally Restricted and Optically Pure Analogues of Serine-Proline Dipeptide via Aldol Condensation

Fabio Massimo Bravin^a, Gilberto Busnelli^a, Matteo Colombo^a, Francesco Gatti^b, Leonardo Manzoni*^c, Carlo Scolastico*^a
^a Dipartimento di Chimica Organica e Industriale and Centro Interdisciplinare Studi bio-molecolari e applicazioni Industriali (CISI), Università degli Studi di Milano, Via Venezian 21, 20133 Milano Italy
e-Mail: carlo.scolastico@unimi.it ;
^b Centro Interdisciplinare Studi bio-molecolari e applicazioni Industriali (CISI), c/o Dipartimento di Chimica Organica e Industriale, Università degli Studi di Milano, Via Venezian 21, 20133 Milano Italy
^c C.N.R. - Istituto di Scienze e Tecnologie Molecolari (ISTM), Via Venezian 21, 20133 Milano Italy
Fax: +39(02)50314072; e-Mail: leonardo.manzoni@istm.cnr.it;

Abstract

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Abstract

Parallel synthesis of a small library of hydroxy functionalized bicyclic lactams with optically pure mimicking dipeptide Pro-Ser has been accomplished via aldol condensation of aldehyde 9 with N-BocGlyCO₂Et. The configurations of eight scaffolds were established unambiguously by NMR spectroscopy.

Key words

lactams - bicyclic compounds - peptidomimetics - asymmetric synthesis - aldol reaction

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References

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