Synthetic studies of 1-.BETA.-methylcarbapenem antibiotics.
- 1 January 1989
- journal article
- research article
- Published by Japan Antibiotics Research Association in The Journal of Antibiotics
- Vol. 42 (3) , 374-381
- https://doi.org/10.7164/antibiotics.42.374
Abstract
The diastereoselective synthesis of the 1-β-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-oxobenzoxazolm-3-yl)-lmethyl-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.This publication has 1 reference indexed in Scilit:
- Stereoselective aldol condensations via boron enolatesJournal of the American Chemical Society, 1981