Abstract: A novel sequence of highly selective chemical reactions for conversion of 3-Aryl-2-propyn-1-ols into cis-1-Aryl-3-fluoro-1-propene and into D,L-(threo)-1-Aryl-2-acylamido-3-fluoro-1-propanols is disclosed. Preparation of D-(threo)-1-Aryl-2-acylamido-3-fluoro-1-propanol antibacterial agents including the D-(threo)-3-fluoro-3-deoxy derivatives of chloramphenicol and thiamphenicol is also disclosed.

Abstract: There is disclosed the antibacterial 5R,6S,8R-6-(1-hydroxyethyl)-2-(2-carbamoyloxyethylthio)-penem-3-carboxylic acid, its pharmaceutically acceptable salts and metabolizable esters as well as compositions containing them and methods for their use, preferably the sodium salt for parenteral administration.

Abstract: There is disclosed the antibacterial 5R,6S,8R-6-(1-hydroxyethyl)-2-(2-[methylaminocarbonyl]-ethylthio)-penem-3- carboxylic acid, its pharmaceutically acceptable salts and esters as well as compositions containing them and methods for their use.

Abstract: Sodium, Potassium, Phthalidyl and Pivalyloxymethyl (5R,6S,8R)-6-(1-hydroxyethyl)-2-(2-hydroxyethylthio)-penem-3-carboxylates exhibit potent, broad spectrum antibacterial activity, are orally effective and chemically stable.

Abstract: There is disclosed the antibacterial 5R,6S,8R-6-(1-hydroxyethyl)-2-(2-glycylaminoethylthio)penem-3-carboxylic acid, its pharmaceutically acceptable salts and esters as well as compositions containing them and methods for their use.

Abstract: 6-Substituted-hydrocarbon-2-(substituted-thio)penem-3-carboxylic acids and congeners having useful antibacterial activity are disclosed. The compounds are prepared in a reaction sequence starting with a 4-acyloxy-2-azetidinone.

Abstract: Disclosed herein are (5R,6S,8R)-6-(1-hydroxyethyl)-2-(2-fluoroethylthio)-penem-3-carboxylic acid and the metabolisable esters thereof and alkali metal salts thereof, which are potent antibacterial agents.

Abstract: An improved synthetic process for the removal of an allyl group in an allylic ester or an allyloxycarbonyl group in an allylic carbonate or carbamate by reaction with 2-ethylhexanoic acid or an alkali metal salt thereof and a catalytic amount of an organic-soluble palladium complex is disclosed herein.

Abstract: .beta.-Lactams having a substituted hydroxymethylene group at the position .alpha. to the lactam carbonyl group are prepared by reaction of an .alpha.-halo-.beta.-lactam with zinc or zinc amalgam in an anhydrous aprotic medium to produce an intermediate which in situ reacts with an appropriate aldehyde or ketone.Also described are novel penicillins and cephalosporins having useful antibacterial activity.

Abstract: .beta.-Lactams having a substituted hydroxymethylene group at the position .alpha. to the lactam carbonyl group are prepared by reaction of an .alpha.-halo-.beta.-lactam with zinc or zinc amalgam in an anhydrous aprotic medium to produce an intermediate which in situ reacts with an appropriate aldehyde or ketone.Also described are noval penicillins and cephalosporins having useful antibacterial activity.

Abstract: Reaction of 6- or 7-diazo-.beta.-lactams with allylic halides in the presence of a catalytic amount of metallic copper or a copper salt affords 6- or 7-carbon-substituted-.beta.-lactams with the desired stereochemical configuration at the 6- or 7-position. Subsequent reduction with a trialkyl stannane affords useful intermediates for further syntheses affording 6- or 7-carbon-substituted-.beta.-lactams.The present invention relates to a process for the production of 6- or 7-carbon-substituted-.beta.-lactams having the desired stereochemical configuration at the 6- or 7-position. More particularly, this invention provides a process for the preparation of a .beta.-lactam of the formula ##STR1## wherein R.sub.1 is cyano or COOR.sub.2 wherein R.sub.2 is a readily removable ester-forming moiety, hydrogen or an alkali-metal cation;R.sub.3 and R.sub.4 are independently hydrogen, lower alkyl, aryl or aralkyl;Z is a group of the formula ##STR2## wherein R.sub.

Abstract: The process for removing a secondary hydroxyl group from an organic compound having at least one secondary hydroxyl group and having any amino groups protected, comprises the reaction of a reactive ester of said secondary hydroxyl group selected from the group consisting of an O-alkylthioester and an O-alkylselenoester with at least one mole of an organotin hydride, preferably tri-n-butylstannane, in an inert, aprotic solvent at a temperature of at least about 100.degree. C and under an inert atmosphere.The process is particularly useful in removing secondary alcohols in aminoglycoside antibiotics to produce deoxy derivatives thereof having antibacterial activity.Also described are novel O-sec.-alkylthiobenzoate, O-sec.-alkyl-S-methylxanthate, N-(sec.-alkoxythiocarbonyl)-imidazole esters, and di-O-alkylthiocarbonates having at least one secondary O-alkyl group, useful intermediates of the claimed process.

Abstract: 5-Deoxy-4,6-di-O-(aminoglycosyl)-1,3-diaminocyclitols, useful antibacterial agents, are prepared by the reaction of the corresponding 5-O-thioformyl-4,6-di-O-(aminoglycosyl)-1,3-diaminocyclitol having all amino functions and all primary and secondary hydroxyl groups protected, with an organotin hydride (preferably tri-n-butylstannane) in an inert aprotic solvent under an inert atmosphere at temperatures of at least about 100.degree. C, followed by removal of said hydroxyl and amino protecting groups.