A new strategy for the synthesis of carbapenems. A formal total synthesis of (+)-thienamycin

A new approach to formation of the carbapenem ring system is presented. The key step involves the Lewis acid mediated cyclocondensation of a β-lactam nitrogen and the α-keto ester of a suitably disposed side-chain. The preparation of a known and pivotal intermediadate in the synthesis of thienamycin...

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Bibliographic Details
Published inTetrahedron letters Vol. 34; no. 30; pp. 4747 - 4750
Main Author Feigelson, Gregg B.
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 23.07.1993
Elsevier
Subjects
Chemistry
Chemistry, Organic
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with only one n hetero atom and condensed derivatives
Organic chemistry
Physical Sciences
Preparations and properties
Science & Technology
ROUTE
ANTIBIOTICS
PENEMS
THIENAMYCIN
Lewis acid
Penicillin derivatives
Intramolecular reaction
Cyclization
Angular nitrogen heterocycle
Enethiol sulfide
Lactam
Bicyclic compound
Aminosulfide
Ketoester
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Summary:A new approach to formation of the carbapenem ring system is presented. The key step involves the Lewis acid mediated cyclocondensation of a β-lactam nitrogen and the α-keto ester of a suitably disposed side-chain. The preparation of a known and pivotal intermediadate in the synthesis of thienamycin serves to demonstrate this strategy. A new approach to formation of the carbapenem ring system is presented. The key step involves the acid mediated reaction of a β-lactam nitrogen and an α-keto ester side-chain. A formal total synthesis of thienamycin serves to demonstrate this strategy.
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(00)74078-0