Cephalosporins to carbapenems: 1-oxygenated carbapenems and carbapenams.

Abstract:

:The photo "Wolff" rearrangement of readily available 2-diazoceph-3-em oxides (1) directly affords carbapen-2-ems, allowing a facile entry into a ring system previously accessible only by total synthesis, lengthly semisynthesis or fermentation. The chirality of the cephalosporin is accurately translated into the corresponding carbapenem. The resulting 1-oxocarbapenems (2) were selectively transformed through reduction into 1-oxygenated carbapenems and carbapenams (3 and 4, respectively). On microbiological screening, a carbapenem (3c) was found to possess a broad spectrum of activity. An interesting antibacterial profile was discovered for a carbapenam (26).

journal_name

J Med Chem

authors

Rosati RL,Kapili LV,Morrissey P,Retsema JA

doi

10.1021/jm00163a048

subject

Has Abstract

pub_date

1990-01-01 00:00:00

pages

291-7

issue

1

eissn

0022-2623

issn

1520-4804

journal_volume

33

pub_type

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