Synthetic studies of 1-beta-methylcarbapenem antibiotics.
The diastereoselective synthesis of the 1-beta-methylcarbapenems, (1R,5R,6S)-6-((R)-1-hydroxyethyl)-2-((S)-1-acetimidoylpyrrolidin-3 - ylthio)-1- methyl-1-carbapen-2-em-3-carboxylic acid and sodium (1R,5R,6S)-6-((R)-1-hydroxyethyl)-2-(5-chloro-2-oxobenzoxazolin-3- y l)-1- methyl-1-carbapen-2-em-3-carboxylate has been achieved. The key step was an aldol reaction between the achiral boron enolate which was generated from dibutylboron triflate and 3-propionyl-2-oxobenzoxazoline, and (3R,4R)-4-acetoxy-3-((R)-1-hydroxyethyl)azetizin-2-one.
Shibata
T
T
Bioscience Research Laboratories, Sankyo Co., Ltd., Tokyo, Japan.
Sugimura
Y
Y
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D015780:Carbapenems; D013845:Thienamycins / Q000138:chemical synthesis* / Q000494:pharmacology
D000900:Anti-Bacterial Agents; D015780:Carbapenems; D013845:Thienamycins; C059382:6-(1-hydroxyethyl)-2-(1-acetimidoylpyrrolidin-3-ylthio)-1-methyl-1-carbapen-2-em-3-carboxylic acid; C059383:6-(1-hydroxyethyl)-2-(5-chloro-2-oxobenzoxazolin-3-yl)-1-methyl-1-carbapen-2-em-3-carboxylic acid