Stereoselective Synthesis of a Functionalized 2-Oxo-1-azabicyclo[5.3.0]alkane as a Potential Scaffold for Targeted Chemotherapy Strategies

Antonio Bracci; Leonardo Manzoni; Carlo Scolastico

doi:10.1055/s-2003-42400

PAPER

Stereoselective Synthesis of a Functionalized 2-Oxo-1-azabicyclo[5.3.0]alkane as a Potential Scaffold for Targeted Chemotherapy Strategies

Antonio Bracci^a, Leonardo Manzoni*^b, 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 Istituto di Scienze e Tecnologie Molecolari (ISTM), Via Venezian 21, I-20133 Milano, Italy
Fax: +39(02)50314072; e-Mail: Leonardo.manzoni@istm.cnr.it;

Abstract

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Abstract

A stereoselective synthesis of functionalized 2-oxo-1-azabicyclo[5.3.0]alkane is presented. Key events of the synthetic sequence were the stereoselective propenylation of an N-acyliminium ion and a ring-closing metathesis reaction forming a 7-membered lactam.

Key words

metathesis - ring closure - lactams - bicyclic compounds - asymmetric synthesis - peptides

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