e.g. Filippa Pettersson or Cancer Res. 75(6) , 1102-12, (2015) or 10.1002/anie.201600521

An enantioselective synthesis of loracarbef (LY163892/KT3777)

CC Bodurow, BD Boyer, J Brennan, CA Bunnell…

Index: Bodurow, C. C.; Boyer, B. D.; Brennan, J.; Bunnell, C. A.; Burks, J. E.; et al. Tetrahedron Letters, 1989 , vol. 30, # 18 p. 2321 - 2324

Full Text: HTML

Citation Number: 62

Abstract

Download full text in PDF Opens in a new window. Article suggestions will be shown in a dialog on return to ScienceDirect. ... Please enable JavaScript to use all the features on this page. ... An enantioselective synthesis of the new, orally absorbable, totally synthetic β-lactam antibiotic, loracarbef (LY163892/KT3777) is described. ... Satisfactory spectral and analytical data were obtained for all new compounds; the diastereomeric excess for compound 11 ...

N-((2R,3S)-2-(2-(furan-2-yl)ethyl)-4-oxoazetidin-3-yl)-2-phenoxyacetamide Structure

N-((2R,3S)-2-(2...

~%

cis-β,4-dioxo-3-[(phenoxyacetyl)amino]-2-azetidinepentanoic acid, (4-nitrophenyl)methyl ester Structure

cis-β,4-dioxo-3...

Mg(mono-PNB malonate)2 Structure

Mg(mono-PNB mal...

cis-4-oxo-3-[(phenoxyacetyl)amino]-2-azetidinepropanoic acid Structure

cis-4-oxo-3-[(p...

~%

cis-β,4-dioxo-3-[(phenoxyacetyl)amino]-2-azetidinepentanoic acid, (4-nitrophenyl)methyl ester Structure

cis-β,4-dioxo-3...

N-((2R,3S)-2-(2-(furan-2-yl)ethyl)-4-oxoazetidin-3-yl)-2-phenoxyacetamide Structure

N-((2R,3S)-2-(2...

~80%

cis-4-oxo-3-[(phenoxyacetyl)amino]-2-azetidinepropanoic acid Structure

cis-4-oxo-3-[(p...

p-nitrobenzyl 7β-[(phenoxyacetyl)amino]-3-hydroxy-1-carba-1-dethia-3-cephem-4-carboxylate Structure

p-nitrobenzyl 7...

~74%

carbacephalosporin hydrochloride Structure

carbacephalospo...

N-((2R,3S)-2-(2-(furan-2-yl)ethyl)-4-oxoazetidin-3-yl)-2-phenoxyacetamide Structure

N-((2R,3S)-2-(2...

~%

carbacephalosporin hydrochloride Structure

carbacephalospo...

cis-α-diazo-β,4-dioxo-3-[(phenoxyacetyl)amino]-2-azetidinepentanoic acid,(4-nitrophenyl)methyl ester Structure

cis-α-diazo-β,4...

~%

carbacephalosporin hydrochloride Structure

carbacephalospo...

cis-β,4-dioxo-3-[(phenoxyacetyl)amino]-2-azetidinepentanoic acid, (4-nitrophenyl)methyl ester Structure

cis-β,4-dioxo-3...

~%

carbacephalosporin hydrochloride Structure

carbacephalospo...

cis-β,4-dioxo-3-[(phenoxyacetyl)amino]-2-azetidinepentanoic acid, (4-nitrophenyl)methyl ester Structure

cis-β,4-dioxo-3...

~88%

cis-α-diazo-β,4-dioxo-3-[(phenoxyacetyl)amino]-2-azetidinepentanoic acid,(4-nitrophenyl)methyl ester Structure

cis-α-diazo-β,4...

N-((2R,3S)-2-(2-(furan-2-yl)ethyl)-4-oxoazetidin-3-yl)-2-phenoxyacetamide Structure

N-((2R,3S)-2-(2...

~%

cis-α-diazo-β,4-dioxo-3-[(phenoxyacetyl)amino]-2-azetidinepentanoic acid,(4-nitrophenyl)methyl ester Structure

cis-α-diazo-β,4...

cis-4-oxo-3-[(phenoxyacetyl)amino]-2-azetidinepropanoic acid Structure

cis-4-oxo-3-[(p...

~%

cis-α-diazo-β,4-dioxo-3-[(phenoxyacetyl)amino]-2-azetidinepentanoic acid,(4-nitrophenyl)methyl ester Structure

cis-α-diazo-β,4...

cis-4-oxo-3-[(phenoxyacetyl)amino]-2-azetidinepropanoic acid Structure

cis-4-oxo-3-[(p...

~%

carbacephalosporin hydrochloride Structure

carbacephalospo...

cis-α-diazo-β,4-dioxo-3-[(phenoxyacetyl)amino]-2-azetidinepentanoic acid,(4-nitrophenyl)methyl ester Structure

cis-α-diazo-β,4...

~75%

p-nitrobenzyl 7β-[(phenoxyacetyl)amino]-3-hydroxy-1-carba-1-dethia-3-cephem-4-carboxylate Structure

p-nitrobenzyl 7...

N-((2R,3S)-2-(2-(furan-2-yl)ethyl)-4-oxoazetidin-3-yl)-2-phenoxyacetamide Structure

N-((2R,3S)-2-(2...

~%

p-nitrobenzyl 7β-[(phenoxyacetyl)amino]-3-hydroxy-1-carba-1-dethia-3-cephem-4-carboxylate Structure

p-nitrobenzyl 7...

cis-4-oxo-3-[(phenoxyacetyl)amino]-2-azetidinepropanoic acid Structure

cis-4-oxo-3-[(p...

~%

p-nitrobenzyl 7β-[(phenoxyacetyl)amino]-3-hydroxy-1-carba-1-dethia-3-cephem-4-carboxylate Structure

p-nitrobenzyl 7...

N-((2R,3S)-2-(2-(furan-2-yl)ethyl)-4-oxoazetidin-3-yl)-2-phenoxyacetamide Structure

N-((2R,3S)-2-(2...

~%

(6R,7S)-4-nitrobenzyl 3-chloro-7-((R)-2-((4-methoxy-4-oxobut-2-en-2-yl)amino)-2-phenylacetamido)-8-oxo-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate Structure

(6R,7S)-4-nitro...

p-nitrobenzyl 7β-[(phenoxyacetyl)amino]-3-hydroxy-1-carba-1-dethia-3-cephem-4-carboxylate Structure

p-nitrobenzyl 7...

~%

(6R,7S)-4-nitrobenzyl 3-chloro-7-((R)-2-((4-methoxy-4-oxobut-2-en-2-yl)amino)-2-phenylacetamido)-8-oxo-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate Structure

(6R,7S)-4-nitro...

cis-4-oxo-3-[(phenoxyacetyl)amino]-2-azetidinepropanoic acid Structure

cis-4-oxo-3-[(p...

~%

(6R,7S)-4-nitrobenzyl 3-chloro-7-((R)-2-((4-methoxy-4-oxobut-2-en-2-yl)amino)-2-phenylacetamido)-8-oxo-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate Structure

(6R,7S)-4-nitro...

cis-α-diazo-β,4-dioxo-3-[(phenoxyacetyl)amino]-2-azetidinepentanoic acid,(4-nitrophenyl)methyl ester Structure

cis-α-diazo-β,4...

~%

(6R,7S)-4-nitrobenzyl 3-chloro-7-((R)-2-((4-methoxy-4-oxobut-2-en-2-yl)amino)-2-phenylacetamido)-8-oxo-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate Structure

(6R,7S)-4-nitro...

cis-β,4-dioxo-3-[(phenoxyacetyl)amino]-2-azetidinepentanoic acid, (4-nitrophenyl)methyl ester Structure

cis-β,4-dioxo-3...

~%

(6R,7S)-4-nitrobenzyl 3-chloro-7-((R)-2-((4-methoxy-4-oxobut-2-en-2-yl)amino)-2-phenylacetamido)-8-oxo-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate Structure

(6R,7S)-4-nitro...