Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
Synthetic Studies of Carbapenem and Penem Antibiotics. III. A Synthesis of a Key Intermediate for 1β-Methylcarbapenem
Akira SASAKIHaruki MATSUMURATsuneo YANOShinji TAKTAMakoto SUNAGAWA
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1992 Volume 40 Issue 5 Pages 1098-1104

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Abstract

We synthesized useful intermediates 5 and 6 for 1β- and 1α-methylcarbapenems from 4-carboxy-3-[(R)-1-hydroxyethyl]-2-azetidinone 4-as a starting material by using stereoselective hydrogenation and hydroboration, respectively. A practical synthetic route from 4 to the (3S, 4S)-4-[(R)-1-carboxyethyl]-3-[(R)-1-hydroxyethyl]-2-azetidinone derivative 1, a useful intermediate for the synthesis of 1β-metylcarbapenem antibiotics, was established.

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© The Pharmaceutical Society of Japan
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