Synthesis 2003(15): 2363-2367  
DOI: 10.1055/s-2003-42400
PAPER
© Georg Thieme Verlag Stuttgart · New York

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

Antonio Braccia, 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;
Further Information

Publication History

Received 20 June 2003
Publication Date:
29 September 2003 (online)

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.