18 天然物をリード化合物とする生理活性物質へのアプローチ : Synthon "Cyanoformate"を用いる合成

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There are some interesting compounds originated from nature, biologically important and containing a partial structure derived from cyanoformate. For instance, kasugamycin(1), penicillin(2), cephalosporin(3), thienamycin(4), virazole(5), orotic acid(6) and an enzyme inhibitor(7) contain such a structural moiety as shown in the figures by dotted lines. The object of the present research is to find a new methodology for the synthesis of such compounds starting from cyanoformate or its correspondents as synthon. The following results were obtained and the experimental conditions were disclosed. 1. Cyanoformates were obtained in good to excellent yields from the reaction of chloroformate and sodium cyanide in the presence of phase-transfer reagents as exemplified in equation 6 (Table 1). 2. N-Substituted carbamimidoylformic acids were obtained in excellent yields under very mild condition from the reaction of an activated form of thiooxamidate with triethyloxonium fluoroborate and various amines as shown in equation 10 (Table 2). For instance, 1 was obtained in 95% yield from 9. 3. The base part of virazole was obtained in excellent yield from the reaction of 8 with formylhydrazine followed by thermal cyclization, and the regiospecific preparation of virazole is now in progress. 4. C-C Bond formation was achieved to afford 16 in excellent yield from the reaction of ethyl cyanoformate and ethyl acetoacetate in the presence of zinc chloride and triethylamine as shown in equation 16 (Table 3).
1978-08-22

18 天然物をリード化合物とする生理活性物質へのアプローチ : Synthon "Cyanoformate"を用いる合成

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