Pyrazine骨格を有する天然物の合成
1997 年 117 巻 1 号 p. 32-48
詳細
1997 年 117 巻 1 号 p. 32-48
This review chiefly describes the syntheses of naturally occurring hydroxypyrazines. First, typical hydroxamic acid type pyrazines such as aspergillic acid, neoasperegillic acid, pulcherriminic acid, and their derivatives are mentioned. Next, synthesis of arglecin and its derivatives, which are hydroxypyrazines carrying with guanidyl group on the side chain, via base-mediated elongation reaction of the carbon skeleton of the 2, 5-dialkylpyrazines are described. Third, synthesis and structural revision of emehetelone, a methoxy-hydroxypyrazine, are included. Septorine, an antibiotic agent from Streptomyces nodorum, is a methoxy-hydroxypyrazine carrying with an aroyl group on the pyrazine ring. The synthesis of septorine was accomplished by utilization of the selective PMA (permaleic acid) oxidation of the chloropyrazine. Further, OPC-15161 and astechrome, which are hydroxypyrazine and pyrazinyl hydroxamic acid, respectively, carrying pyrazine and indole rings, were prepared. Finally, syntheses of terramide A, B, and C, cyclic bishydroxamic acid type piperazines, via the reduction of 2, 5-dihydroxypyrazine 1, 4-dioxides are described.
