Synthesis of 3-Hydroxycephems from Penicillin G through Cyclization of Chlorinated 4-(Phenylsulfonylthio)-2-azetidinones Promoted by a BiCl3/Sn or TiCl4/Sn Bimetal Redox System

doi:10.1246/BCSJ.68.1385

Paper

Synthesis of 3-Hydroxycephems from Penicillin G through Cyclization of Chlorinated 4-(Phenylsulfonylthio)-2-azetidinones Promoted by a BiCl3/Sn or TiCl4/Sn Bimetal Redox System

Published May 1, 1995 · Hideo Tanaka, M. Taniguchi, Y. Kameyama

Bulletin of the Chemical Society of Japan

Q2 SJR score

9

Citations

0

Influential Citations

Full textSemantic Scholar

Abstract

A novel access to 3-hydroxycephems was attained from penicillin G via the C=C bond cleavage of 1-(1-alkoxycarbonyl-2-chloromethyl-2-propenyl)-4-(phenylsulfonylthio)-2-azetidinones by successive treatment with RuCl3/HIO4 and HIO4/CuSO4 and reductive cyclization of 1-(1-alkoxycarbonyl-3-chloro-2-hydroxy-1-propenyl)-4-(phenylsulfonylthio)-2-azetidinones on treatment with a newly devised BiCl3/Sn or TiCl4/Sn bimetal redox couple in DMF containing pyridine.

Study Snapshot

This novel method allows for the synthesis of 3-hydroxycephems from penicillin G by cleaving C=C bonds and reductive cyclization of chlorinated 4-(phenylsulfonylthio)-2-azetidinones in a BiCl3/S

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

Sign up to use Study Snapshot

Consensus is limited without an account. Create an account or sign in to get more searches and use the Study Snapshot.

Create an account

Paper

Synthesis of 3-Hydroxycephems from Penicillin G through Cyclization of Chlorinated 4-(Phenylsulfonylthio)-2-azetidinones Promoted by a BiCl3/Sn or TiCl4/Sn Bimetal Redox System

Sign up to use Study Snapshot

References

Studies on beta-lactam antibiotics VIII. Structure-activity relationships of 7 beta-[(Z)-2-carboxymethoxyimino-2-arylacetamido]-3-cephem- 4-carboxylic acids.

7 beta-[(Z)-2-carboxymethoxyimino-2-arylacetamido]-3-cephem-4-carboxylic acids show promising antimicrobial activity and oral absorptivity, with the [(Z)-2-(2-amino-4-thi

Penicillin-cephalosporin conversion III. A Novel route to 3-chloromethyl-Δ3-cephems

This novel route to 3-chloromethyl-3-cephems from penicillins G and V enables the conversion of penicillins into cephalosporins with minimal environmental impact.

Neue β‐Lactam‐Antibiotika. Über Derivate der 3‐Hydroxy‐7‐amino‐ceph‐3‐em‐4‐carbonsäure. Modifikationen von Antibiotika, 10. Mitteilung [1]

New -lactam antibiotics can be prepared by ozonolysis of 3-hydroxy-ceph-3-em-esters, which can be transformed into various acids and derivatives by various transformations of the -ketoester system.

Chemoselective electrolytic chlorination of methyl group of 3-methyl-3-butenoate moiety of thiazoline-azetidinone homologues

Chemoselective electrolytic chlorination of the methyl group in thiazoline-azetidinone derivatives from penicillins G and V can be achieved by adjusting electricity and Cl concentration in the media.

Reduction of cephalosporanic acids with chromium(II) salts : Synthesis of 3-methylenecepham derivatives

Chromium(II) salts can convert 7-acylaminocephalosporanic acid derivatives into 3-methylenecepham-4-carboxylic acids, which can be easily isomerized to 3-methyl-3-cephem compounds under basic conditions.

Citations

Stereoselective Synthesis of Tricyclic β-Lactam by Sulfoxide-Directed Oxidative Lactonization from an Accessible Cephalosporin Intermediate.

This study successfully synthesized the key intermediate for tricyclic -lactam antibiotics from an accessible and inexpensive cephalosporin intermediate in six steps, achieving 23% total yield in six steps.

Patent Review of Manufacturing Routes to Fifth-Generation Cephalosporin Drugs. Part 2, Ceftaroline Fosamil and Ceftobiprole Medocaril

Ceftaroline fosamil and ceftobiprole medocaril are effective against serious bacterial infections, including MRSA, and their patent literature provides insights into synthetic routes and final forms.

PROCESS FOR THE PRODUCTION OF β-LACTAM COMPOUNDS

The process for producing halogenated -lactam compounds involves replacing hydroxyl groups with halogen atoms or leaving groups, and reducing halogenated -lactam compounds with metal compounds having higher oxidation-reduction potentials.

Synthesis of 2-exo-Methylenepenam by Reductive 1,2-Elimination and S–S Bond Fission in a PbBr2/Al Bimetal System

This method allows for the efficient synthesis of 2-exo-methylenepenam from penicillin G by reductive elimination of chlorine atoms and/or triflate moiety and S-S bond fission in a PbBr2/Al bimetal system.

Conversion of cephem into penam/penem through sequential ring-opening/recyclization in an Al/BiCl3/AlCl3 system

This study successfully converted cephem into penam/penem by sequential ring-opening/recyclization in an Al/BiCl3/AlCl3 system, with 3-norcephalosporin as a major product when the reaction was performed in methanol.

Construction of cephem framework via sequential reductive 1,2-elimination–hydride addition in a tributyltin hydride–copper(I) chloride–NMP system: synthesis of 3-norcephalosporin

This study successfully synthesized 3-norcephalosporin using tributyltin hydride, copper(I) chloride, and NMP, demonstrating its potential as a cephem framework.