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An efficient enantioselective synthesis of the carbapenam-2-one system. An approach to (+)-thienamycin and related carbapenems

✍ Scribed by A.I. Meyers; Thomas J. Sowin; Stefan Scholz; Yasutsugu Ueda

Publisher: Elsevier Science
Year: 1987
Tongue: French
Weight: 215 KB
Volume: 28
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)95602-8

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✦ Synopsis

Cycloaddition of the enantiomeric 4-acetoxy-2-azetidinone (5) with the 2-siloxy-1,3butadiene (8) gives the carbacephem 9 which is cleaved via ozone and cyclized to the carbapenem system (+)-13 in 30% overall yield. The extensive activity directed toward the carbapenem systems (1, 2) due to their highly important antibiotic properties, 2 has resulted in a large number of synthetic achievements.3 In fact, the P-methyl derivative 2 is currently considered the flagship of the new generation of potent and stable carbapenems.4

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