Crysanthemic acid

The structure consists of a crysanthemic acid nucleus and m.phenoxy (cyano)benzyl alcohol (PCBA). 

The main products with this structure are fenvalerate, esfenvalerate, flucythrinate and fluvalinate all of which do not have a crysanthemic acid derivate. 

The isocyanates (9) were transformed into amino derivatives by standard reactions. Acid-sensitive aminocyclopropanes were obtained preferentially from benzyr ) -naphthyl or trifluorethyl-urethanes which were cleaved by hydrogen, EtSNa/DMF or alkaline hydrolysis. The hydrazinolysis of phthalimido compounds obtained from the urethane and phthalic anhydride also was useful Trimethylsilylethanol proved to be advantageous for the isocyanate-amine conversion the resulting urethanes gave amines upon addition of Bu4N p- 161 (e.g. synthesis of amine (21) from truns-crysanthemic acid via isocyanate (20) S equation 3). Contrarily to... 

Transition metal salts or complexes are known to catalyze effectively the cyclopropanation of olefins with diazoalkanes. Asymmetric synthesis with chiral copper catalysts (Nozaki et ai, 1966, 1968 Noyori et al., 1969 Moser, 1969), as well as a detailed kinetic study (Salomon and Kochi, 1973), has suggested the intervention of copper-carbene complexes as reactive intermediates. Recently synthesis of crysanthemic acid (CCXXXIV) (R = H) with high optical yield (60-70 %) has been achieved by applying this asymmetric catalysis (Aratani et al., 1975). The camphorglyoxime-cobalt(I) complex is also effective for the enantioselective reaction (Tatsuno et al., 1974). 

In the past year, (+)- a -crysanthemic acid has been prepared from a number of readily available chiral monoterpenes, namely (—)-carvone, (+)-limonene, a-terpineol, and (+)-3-carene. Furthermore, an asymmetric synthesis of (liJ)-cw-permethric acid (11) has been achieved by the reaction of 1-menthyl diazoacetate and l,l-dichloro-5-methylpenta-l,3-diene in the presence of the... 

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