Cavalla

Cavalla, J.F. and White, A.C. British Patent 1,285,025 August 9,1972 assigned to John Wyeth Brother Ltd. 

Atlantic mackerel, Scomber scombrus, liver King mackerel, Scomberomorus cavalla, otolith 31 FW 14... 

Grady, J.R., A.G. Johnson, and M. Sanders. 1989. Heavy metal content in otoliths of king mackerel (Scomb-eromorus cavalla) in relation to body length and age. Contrib. Mar. Sci. 31 17-23. 

A dinoflagellate, Gambierdiscus toxicus has been reported to be the likely progenitor of ciguatoxin in the South Pacific (13-15). Recently, Tindall, (26), Miller, ]]) and Carlson, (18) reported on toxic extracts from G. toxicus and two species of Prorocentrum from the Caribbean. iHe physiological action of toxic extracts from G, toxicus were found to be similar to those induced by toxic extract from Scomberomorus cavalla (Kingfish) from the same region (19). 

Synthesis (Cavalla and White (Wyeth), 1969 1969 Bradley 1980 Kleemann et al. 1999) By condensation of 2-(m-methoxyphenyl)butyronitrile with ethyl 4-iodobutyrate by means of NaNH2 in liquid NH3 to give ethyl 5-cyano-5-(m-methoxyphenyl)heptanoate, which is cyclized by hydrogenation with H2 over Raney Ni in cyclohexane to yield 6-ethyl-6-(m-methoxyphenyl)hexahydro-2H-azepin-2-one this ketone is reduced with LiAIH4 in THF to 3-ethyl-3-(m-methoxyphenyl)hexahydro-IH-azepine, which in turn, is reductively methylated with HCHO, H2 and Pd/C in ethanol to give 1-methyl-3-ethyl-3-(m-methoxyphenyl)-hexahydro-1H-azepine, and finally demethylated by refluxing with 80% HBr to yield a racemic mixture of the final product. 

B-81MI10602 Risk-Benefit Analysis in Drug Research , ed. J. F. Cavalla M.T.P. Press,... 

---