Synthesis 2012; 44(18): 2825-2839
DOI: 10.1055/s-0032-1316732
feature article
© Georg Thieme Verlag Stuttgart · New York

An Entry to the Carbapenem Antibiotic Scaffold via the Asymmetric Kinugasa Reaction

Magdalena Maciejko
Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, Poland, Fax: +48(22)6326681   Email: chmiel@icho.edu.pl
,
Sebastian Stecko
Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, Poland, Fax: +48(22)6326681   Email: chmiel@icho.edu.pl
,
Olga Staszewska-Krajewska
Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, Poland, Fax: +48(22)6326681   Email: chmiel@icho.edu.pl
,
Margarita Jurczak
Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, Poland, Fax: +48(22)6326681   Email: chmiel@icho.edu.pl
,
Bartłomiej Furman
Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, Poland, Fax: +48(22)6326681   Email: chmiel@icho.edu.pl
,
Marek Chmielewski*
Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, Poland, Fax: +48(22)6326681   Email: chmiel@icho.edu.pl
› Author Affiliations
Further Information

Publication History

Received: 28 April 2012

Accepted after revision: 04 July 2012

Publication Date:
13 August 2012 (eFirst)

Abstract

The copper(I)-mediated reaction between five-membered cyclic nitrones and terminal acetylenes, leading to the assembly of the basic skeleton of carbapenem antibiotics is described. The diastereoselectivity of this cycloaddition–rearrangement cascade, a process known as the Kinugasa reaction, with respect to the structure and configuration of both substrates, as well as the reaction conditions, are discussed. Application of the described methodology to sugar-derived nitrones offers an attractive entry toward thienamycin and related compounds.

Supporting Information

 
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