By M. S. Newman, B. Tierney, S. Veeraraghavan
First released in 1988, this quantity surveys the chemical synthesis and organic task of the benz[a]anthracenes. those compounds ensue in smoke and mineral oils and some were proven to be powerful cancer causing agents. This quantity used to be the 1st to study, systematically and extensive, the natural synthesis of those compounds in addition to their metablolism, interactions with nucleic acids and protein, mutagenicity and carcinogenicity. Such experiences have very important implications in opting for mechanism and specificity of chemically brought on carcinogenesis.
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32 Chemistry Scheme 2XEZ. Diels-Alder Reactions of 1,4-Naphthoquinone. OR 0 OR 0 204(R=H) 2O5(R=CH3) 202 (R = H) 203(R = CH3) 2J0 2JJ. 2J2 2J3 (R=H),9-pos (R=CH3),9-pos (R=H), 10-pos (R=CH3),IO-pos 206 (R = H) 207(R=CH3) R ^ ( = H,R'=N(CH3)259% 2I5(R=H,RI=OCH3)I4O% U | ( R = 04^^(013)2), 16% Synthesis of l-MeO-4-MBAQ is particularly interesting because it illustrates the introduction of the sterically hindering methoxy group. By the reaction of 5-methoxy-2-methylstyrene, 217 (Kelly et ai, 1980), with 202 ll-hydroxy-l-methoxy-4-methylBAQ, 218, was synthesized, Scheme XXV.
1981), for such closures has also been reported. By reduction of 155 and aromatization, BA was obtained. Similarly 158 yielded 9MBA and by reaction of 158 with methylmagnesium iodide followed by aromatization, 8,9-DMBA was produced. The latter hydrocarbon was of interest in establishing the structure of methylcholanthrene (Cook and Haslewood, 1934). The condensation of succinic anhydride with 3-methylphenanthrene afforded /3-[6-(3-methylphenanthroyl)]propionic acid, 159, from which 2-MB A was synthesized by conventional steps (Bachmann and Cortes, 1943).
Acylation of Phenanthrenes. RCH2 -MBA S \_79 CO2H 180 a. bromination b. NaCH(CO 2 C2H 5 ) 2 c. hydrolysis d. decarboxylation e. reduction f. ring closure CH 3 OH, Ag 2 O k. SnCI 4 h. SOCL i. CHJVL g. HBr I. Pd-C of the keto group and ring closure led to 8-keto-8,9,10,ll-tetrahydro-10MBA, 174, and from it 10-MBA and 8,10-DMBA were synthesized (Bachmann and Chemerda, 1938). Starting from the condensation product of 3-acetylphenanthrene with diethyl succinate and treatment of the first formed half-ester with hydrobromic acid there was obtained 30 Chemistry the lactone 175.