Deoxyaspergillic acids

The procedure was successfully applied to the synthesis of deoxyaspergillic acid [ 114]... 

Cyclizine, l-(diphenyhnethyl)-4-methylpiperazine (hydrochloride or tartrate), histamine Hrreceptor antagonist sedative and antiemetic [82-92-8], Deoxyaspergillic acid (H 50, 158), 6-.scc-butyl-3-isobutyl-2(l//)-pyrazinonc, an Aspergillus sp metabolite 121641 -71-4],122 980 Deoxymutaaspergillic acid (H 158, 193), 3-isobutyl-6-isopropyl-2(l//)-pyrazi-none, an Aspergillus sp metabolite [22318-05-4],122... 

This reaction gives good results for a variety of activated and unactivated alkyl hahdes [112] Oxidation of 2-bromoketones with N-phenyltriflaimde was used in a one pot synthesis of pyrazmes by the sequence of reactions shown m equaUon 57 [113] The procedure was successfully applied to the synthesis of deoxyaspergillic acid [ I14 ... 

Bromination of 5-s-butyl-3-hydroxy-2-isobutylpyrazine (deoxyaspergillic acid) in aqueous solution or acetic acid gave 2-bromo-3-s-butyl-5-hydroxy-6-isobutylpyrazine (bromodeoxyaspergjllic acid) (87) bromination of 2-s-buty-3-hydroxy-5-isobutyl-pyrazine in acetic acid gave 2-bromo-6-s-butyl-5-hydroxy-3-isobutylpyrazine (93) and 3-hydroxy-2,5-diphenylpyrazine behaved similarly (282). This procedure with bromine in acetic acid was unsatisfactory when applied to simpler hydroxypyrazines (817), and bromination of 3,6(and 5,6)-disubstituted-2-hydroxypyrazines and 2-... 

Deoxyaspergillic acid was also produced from aspergillic acid by refluxing in acetic acid with red phosphorus and hydriodic acid, and by dry distillation with copper-chromite catalyst (86). Reduction of 2,5-dihydroxy-3,6-diisobutylpyrazine 1,4-dioxide (pulcherriminic acid) with red phosphorus and iodine in refluxing acetic... 

A new synthesis of deoxyaspergillic acid (266) exemplifies the use of N-phenyltriflamide (PhNHS02Cp3) in pyrazine synthesis (Scheme 106). The con-NO... 

Newbold, G. T., W. Sharp, and F. S. Spring Aspergillic acid. Part III. The synthesis of racemic deoxyaspergillic acid. J. Chem. Soc. 1951, 2679. 

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