Martel synthesis

The process for the industrial production of permethric acid by Roussel-Uclaf starts from racemic trons-chrysanthemic acid, which is in turn accessed by the Martel synthesis (cf. 1,3-cycloelimination). After separation of the enantiomers with an amino-alcohol, the (IR)-enantiomer is subjected to ozonolysis. Basic epimerisation gives (IR)-cis-caronaldehyde hemiacetal. Water is added to the (IS)-enantiomer in the presence of a catalytic amount of sulfuric acid then the carboxylic add function is epimerised with the formation of a lactone. Magnesium bromide-catalysed ring-opening leads to (lR)-c s-chrysanthemic acid, which is converted into (IR)-ds-caronaldehyde hemiacetal by an analogous route. [105]... 

The synthesis of the moxifloxacin core (de Souza, 2006 Martel et al., 1997 Seidel et al., 2000) proceeds from a Grohe-Heitzer sequence as described earlier in the chapter. Unlike the traditional Grohe-Heitzer sequence, however, the opening step involved the reaction between acid chloride 101 with the mono potassium salt of malonic acid monoethyl ester (102) in the presence of triethylamine to deliver ketoester 103 (Scheme 4.18). Treatment of 103 with ethyl orthoformate furnished acrylate 104, which reacted with cyclopropyl amine to afford 105. Cyclization of 105 in the presence of sodium fluoride in DMF gave the moxifloxicin core 106. 

J.M. Chapuzet, B. Cot6, M. Lavoie, E. Martel, C. Raffm, and J. Lessard. "The Selective Reduction of Aliphatic and Aromatic Nitro Compounds" in Novel Trends in Electroorganic Synthesis, S. Torii, Ed., Kodansha, Tokyo, 1995, p. 

Martell et al. (33g) while studying the complex equilibria of a new octaaza macrobicyclic cryptand, (MX)3(tren)2 (containing two tren moieties and three m-xylyl groups) reported the synthesis and... 

Wang, Z. Reibenspies, J. Martell, A. E. Design, synthesis and X-ray structural characterization of new dinucleating macrocyclic ligands and a novel phenolate-bridged dilanthanum(III) complex. Inorg. Chem. 1997, 36, 629-636. 

Martell AE (1981) The design and synthesis of chelating agents. In Martell AE, Anderson WF, Badman DG (eds) Development of Iron Chelators for Clinical Use. Elsevier/North-Holland, New York p 67-104... 

Chen, D. Martell, A. E. The synthesis of new binuclear polyaza macrocyclic and macrobicyclic... 

Martel-Pelletier J, Quinissi H, Cloutier JM, Pellettier JP. Tenidap effectively reduces cytochine synthesis and expression by human rheumatoid arthritis synovium. Arth Rheum 1994 37. 

Le Thuaut Ph., Martel B., Crini G., Maschke U., Martel B., Coqueret X., Morcellet M., Grafting of cyclodextrins onto polypropylene nonwoven fabrics for the manufacture of reactive filters - Part 1 Synthesis parameters, J. Appl. Polym. Sci., 2000,77,21 18-2125. 

Jaworski, R., Pierlot, C., Pawlowski, L., Bigan, M., and Martel, M. (2009b) Design of the synthesis of fine hydroxyapatite powder for suspension plasma spraying. Surf. Coat. Technol., 203 (15), 2092-2097. 

The stereoselective synthesis of ( )-ethyl chrysanthemate (17) has been achieved by Martel and Huyne (1967). The crucial step of their process is the addition of phenyl 3-methyl-2-butenyl sulfone to ethyl-3-methacrylate. 

In 1966 Martel and Duffaut [210] and Gronowicz and Ryan [86] reported the first synthesis of 0-triorganosilyl thiocarboxylates 83b from reacting thiocar-boxylic acids with triorganosilyl chlorides or triorganosilylamines, respectively. Since then, several preparation routes have been developed (1) RCOSH or M(RCOS) (M=alkali metal) + R SiCl [144] (2) RCOCl+R 3SiSLi [77] or (R 3Si)2S [202] (3) acyl thiocarbamoyl sulfides + R SiCl in the presence of triethylamine... 

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