Shoichiro Uyeo

Stereocontrolled, straightforward synthesis of 3-substituted methyl 7α-methoxy-1-oxacephems☆

Abstract Stereocontrolled and industrially feasible synthesis of a new antibiotic 1a and related derivatives, which is characterized by using all the carbon atoms of the penicillin skeleton, is described.

A simple and stereocontrolled syntheses of a 1β-methylcarbapenem key intermediate by means of organosilicon chemistry

Abstract A simple and stereocontrolled synthesis of 1 , starting from the acetoxy-azetidinone 5 via N -( Z )-crotylsilane compound 7 , was developed.

Synthetic studies on β-lactam antibiotics. Part 16. synthesis of 1-carba-2-penem-3-carboxylic acid esters from penicillins utilizing a carbon-carbon coupling reaction

Abstract Allylazetidinones 9 , 10 , prepared by coupling of allylcoppers 8 with chloroazetidinones 6 , 7 , were converted into carbapenem esters 16 , 28 – 31 using an Emmons-Horner reaction to introduce the 6-side chain and an intramolecular Wittig reaction to form the carbapenem ring system.

Total synthesis of dl-asparenomycins A, B and C, novel carbapenem antibiotics

Abstract Total synthesis of dl-asparenomycins was accomplished with direct conversion of carbonates 13a, 13b and 14a, 14b to asparenomycin esters 15 and 16 and carboxy deprotection by the AlCl3-anisole method.

Synthesis and antibacterial activity of 2-functionalized-vinyl 1β-methylcarbapenems and related compounds

Abstract The synthesis and antibacterial activity of the title compounds are described. Both 2-hydroxymethyl and 2-hydroxypropenyl carbapenems (3 and 14) served as the common key intermediates for the preparation of these compounds. The characteristic antibacterial activity was observed in the three types (A, B, and C) of derivatives prepared.

Synthetic studies on β-lactam antibiotics. 13. Transformation of 6-epipenicillins to 2R-{(1S, 5R)-2-oxa-6-oxo-4,7- diazabicyclo[3.2.0]hept-3-en-7-yl}-3-methylbut-3-enoates

Abstract Reaction of 2β-unsubstituted or functionalized-methyl 6-epipenicillin sulfoxides 2 with tervalent phosphorus compounds gave azetidinone-epi-oxazolines 3 , important intermediates in synthesis of 7α-methoxy-1-oxacephems. Preparation of the 2β-functionalized-methyl substrates is described also.