Asymmetric hetero Diels-Alder as an access to carbacephams

Alberto Avenoza; Jesús H Busto; Carlos Cativiela; Francisco Corzana; Jesús M Peregrina; María M Zurbano

doi:10.1021/jo016186h

Asymmetric hetero Diels-Alder as an access to carbacephams

J Org Chem. 2002 Jan 25;67(2):598-601. doi: 10.1021/jo016186h.

Authors

Alberto Avenoza¹, Jesús H Busto, Carlos Cativiela, Francisco Corzana, Jesús M Peregrina, María M Zurbano

Affiliation

¹ Departamento de Química, Universidad de La Rioja Grupo de Síntesis Química de La Rioja, U.A.-C.S.I.C., 26006 Logroño, Spain. alberto.avenoza@dq.unirioja.es

PMID: 11798338
DOI: 10.1021/jo016186h

Abstract

A short and efficient asymmetric synthesis of the (6R,7S)-7-tert-butoxycarbonylamino-2-ketocarbacepham is described. The key step involves the hetero Diels-Alder reaction of the benzylimine derived from the enantiomer of Garner's aldehyde with Danishefsky's diene.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Carbapenems / chemical synthesis*
Carbapenems / chemistry*
Catalysis
Cephalosporins / chemical synthesis*
Cephalosporins / chemistry
Chromatography, Thin Layer
Crystallography, X-Ray
Cyclization
Molecular Structure
Nuclear Magnetic Resonance, Biomolecular
Spectrometry, Mass, Electrospray Ionization
Spectrophotometry, Infrared
Stereoisomerism
Structure-Activity Relationship

Substances

7-tert-butoxycarbonylamino-2-ketocarbacepham
Carbapenems
Cephalosporins