Synthetic studies of carbapenem and penem antibiotics. III. A synthesis of a key intermediate for 1 beta-methylcarbapenem.
We synthesized useful intermediates 5 and 6 for 1 beta- and 1 alpha-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 1 beta-methylcarbapenem antibiotics, was established.
Sasaki
A
A
Research Laboratories, Sumitomo Pharmaceuticals Co., Ltd., Osaka, Japan.
Matsumura
H
H
Yano
T
T
Takata
S
S
Sunagawa
M
M
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis*; D015780:Carbapenems / Q000138:chemical synthesis*
D000900:Anti-Bacterial Agents; D015780:Carbapenems