The chemistry of 4-mercaptoazetidin-2-ones. Part 4. Synthesis of cyclopropanespiro-2-bisnorpenicillanic acids
- 1 January 1982
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 7,p. 1435-1439
- https://doi.org/10.1039/p19820001435
Abstract
Reaction of the 4-mercaptoazetidin-2-one (6) with benzyl 2-bromocyclopropylideneacetate (7) gave the C-3 epimeric cyclopropanespiro-2-bisnorpenicillanates (9) and (10). Standard procedures were used to convert the 3S-epimer into the ampicillin analogue (15). Hydrogenolysis of the esters (9) and (15) gave the cyclopropane spiro-2-bisnorpenicillanic acids (13) and (16) both of which had antibacterial properties similar to those of the corresponding penicillins.This publication has 2 references indexed in Scilit:
- Studies related to penicillins and cephalosporins. Part 6. Synthesis of the (±)-dinorpenicillin-spirocyclopentane systemJournal of the Chemical Society, Perkin Transactions 1, 1980
- (±)-Dinorpenicillin-2-spirocycloalkaneJournal of the Chemical Society, Chemical Communications, 1978