102437-18-3

Upstream product

• 6297-22-9 4-carbomethoxycyclohexanone 
• 107-18-6 allyl alcohol 
• 3618-03-9 methyl 4-hydroxycyclohexanecarboxylate 
• 556-56-9 allyl iodid 
• 99-96-7 4-hydroxy-benzoic acid 
• 3685-22-1 4-hydroxycyclohexanecarboxylic acid 
• 106-95-6 allyl bromide 
• 186581-53-3 diazomethane 
• 19207-19-3 1-(2',5'-dioxolanyl)-3,4-epoxycyclohexane 
• 1730-25-2 allylmagnesium bromide 

Downstream Products

• 102437-22-9 (1R,3R,4S)-4-Hydroxy-3-(3-hydroxy-propyl)-cyclohexanecarboxylic acid methyl ester 
• 102437-22-9 (1R,3R,4R)-4-Hydroxy-3-(3-hydroxy-propyl)-cyclohexanecarboxylic acid methyl ester 
• 102437-04-7 (1S,3S,4S)-3-Allyl-4-hydroxy-cyclohexanecarboxylic acid methyl ester 
• 102437-04-7 4(e)-carbomethoxy-cis-2-allylcyclohexanol 
• 102437-33-2 (1S,3R,4R)-3-Allyl-4-formyl-cyclohexanecarboxylic acid methyl ester 
• 102437-33-2 (1R,3R,4R)-3-Allyl-4-formyl-cyclohexanecarboxylic acid methyl ester 
• 102437-33-2 (1S,3R)-3-Allyl-4-formyl-cyclohexanecarboxylic acid methyl ester 
• 102437-22-9 4-carbomethoxy-2-(3-hydroxypropyl)cyclohexanol 
• 102437-23-0 (1R,3S,4R)-3-(3-Hydroxy-propyl)-4-(toluene-4-sulfonyloxy)-cyclohexanecarboxylic acid methyl ester 
• 102437-40-1 (1S,3S,4R)-3-(2-Hydroxy-ethyl)-4-(toluene-4-sulfonyloxymethyl)-cyclohexanecarboxylic acid methyl ester 
• 102437-39-8 (1S,3S,4R)-3-(2-Oxo-ethyl)-4-(toluene-4-sulfonyloxymethyl)-cyclohexanecarboxylic acid methyl ester 
• 102437-37-6 (1S,3R,4R)-3-Allyl-4-(toluene-4-sulfonyloxymethyl)-cyclohexanecarboxylic acid methyl ester 
• 102437-25-2 (1R,3S,4R)-3-Allyl-4-(toluene-4-sulfonyloxy)-cyclohexanecarboxylic acid methyl ester 
• 772298-43-8 (4aS,6R,8aS)-1-Methyl-decahydro-quinoline-6-carboxylic acid methyl ester 

Relevant academic research and scientific papers

Discovery of LFF571: An investigational agent for Clostridium difficile infection

Clostridium difficile (C. difficile) is a Gram positive, anaerobic bacterium that infects the lumen of the large intestine and produces toxins. This results in a range of syndromes from mild diarrhea to severe toxic megacolon and death. Alarmingly, the prevalence and severity of C. difficile infection are increasing; thus, associated morbidity and mortality rates are rising. 4-Aminothiazolyl analogues of the antibiotic natural product GE2270 A (1) were designed, synthesized, and optimized for the treatment of C. difficile infection. The medicinal chemistry effort focused on enhancing aqueous solubility relative to that of the natural product and previous development candidates (2, 3) and improving antibacterial activity. Structure-activity relationships, cocrystallographic interactions, pharmacokinetics, and efficacy in animal models of infection were characterized. These studies identified a series of dicarboxylic acid derivatives, which enhanced solubility/efficacy profile by several orders of magnitude compared to previously studied compounds and led to the selection of LFF571 (4) as an investigational new drug for treating C. difficile infection.

General Syntheses of 6- and 7-Carbomethoxy-trans-1-heteradecalins and 6- and 7-Carbomethoxy-trans-2-heteradecalins

Two routes to all of the title compounds in the oxa and aza series have been studied.The most general path, involving a cyclohexene oxide intermediate, was not successful becauase of difficulty in separating regioisomers.Allylation of 4-carbomethoxycyclohexanone (11) followed by reduction produced the required trans-disubstituted allyl alcohols, which were converted to all of the desired 6-carbomethoxy-trans-1-heteradecalins.The allyl ketones were subjected to a homologation-side chain contraction sequence to produce the 6-carbomethoxy-trans-2-heteradecalins.Allylation of 3-carbomethoxycyclohexanone (12) was not regioselective, but all four product isomers were characterized.The desired 5-carbomethoxy-2-allylcyclohexanone isomers (27 and 28) were converted to the 7-carbomethoxy-trans-decalins by similar series of reactions