Studies on the syntheses of heterocyclic compounds. Part 877. An alternative synthesis of protected (±)-thienamycin and a related compound
- 1 January 1981
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 3,p. 964-968
- https://doi.org/10.1039/p19810000964
Abstract
An alternative total synthesis of protected (±)-thienamycin (2) and an analogue is described. (±)-4β-(2,2-Dimethoxyethyl)-3α-[(1R*)-1-(p-nitrobenzyloxycarbonyloxy)ethyl]azetidin-2-one (5), prepared from isoxazoline derivatives (4), was converted into the 2-(p-nitrobenzyloxycarbonylamino)ethyl (12) and phenyl (13) thioester phosphoranes. Intramolecular Wittig reaction of (12) and (13) produced the corresponding carbapenems (2) and (3) in poor yield. Effective transformation of (5) into the p-nitrobenzyl-protected thienamycin derivative (2) and the analogue (3) was achieved employing a carbene insertion reaction and subsequent introduction of the sulphide moiety.This publication has 13 references indexed in Scilit:
- The penems, a new class of .beta.-lactam antibiotics. 2. Total synthesis of racemic 6-unsubstituted representativesJournal of the American Chemical Society, 1979
- The penems, a new class of .beta.-lactam antibiotics. 4. Syntheses of racemic and enantiomeric penem carboxylic acidsJournal of the American Chemical Society, 1979
- Thienamycin, a new .BETA.-lactam antibiotic. I. Discovery, taxonomy, isolation and physical properties.The Journal of Antibiotics, 1979
- Olivanic acids, a family of .BETA.-lactam antibiotics with .BETA.-lactamase inhibitory properties produced by Streptomyces species. II. Isolation and characterisation of the olivanic acids MM 4550, MM 13902 and MM 17880 from Streptomyces olivaceus.The Journal of Antibiotics, 1979
- Olivanic acids, a family of .BETA.-lactam antibiotics with .BETA.-lactamase inhibitory properties produced by Streptomyces species. I. Detection, properties and fermentation studies.The Journal of Antibiotics, 1979
- PS-5, a new .BETA.-lactam antibiotic. I. Taxonomy of the producing organism, isolation and physico-chemical properties.The Journal of Antibiotics, 1979
- The penems, a new class of .beta.-lactam antibiotics: 6-acylaminopenem-3-carboxylic acidsJournal of the American Chemical Society, 1978
- Structure and absolute configuration of thienamycinJournal of the American Chemical Society, 1978
- PS-5, A new .BETA.-lactam antibiotic from Streptomyces.The Journal of Antibiotics, 1977
- Structure elucidation of MM 17880, a new fused β-lactam antibiotic isolated from Streptomyces olivaceus; a mild β-lactam degradation reactionJournal of the Chemical Society, Chemical Communications, 1977