3 新抗生物貭Tolypomycinの構造

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Tolypomycin Y (C_<43>H_<54>N_2O_<14>, I), which exhibits a strong inhibition against gram positive bacteria, was isolated from Streptomyces tolypophorus. Tolypomycin Y upon redaction with H_2/pt, resulted in tolypomycin R (II), which on oxidation gave I. Mild acid hydrolysis of I afforded an aminosugar, tolyposamine (C_6H_<13>NO_2, III) and a yellow quinone, tolypomycinone (C_<37>H_<43>NO_<13>, IV). III gave the N-benzoyl-O-methyl-derivatives (Va, Vb). The periodate oxidation of III gave acetaldehyde, while the permanganate oxidation led to succinic acid and ammonia. From these results, III is assumed to be 4-amino-2,3,4,6-tetradeoxypyranohexose. When IV was hydrolyzed with acid, a naphthoquinone, 2-amino-8,11-dihydroxy-7,12-dimethyl-11,12-dihydrofuro[3,2-f]-1,4-naphthoquinone-11-one (IX), tolypolide F_1 (C_<22>H_<30>O_7; XIV) and F_2 (XV) were obtained. A γ-lactone, tolypolide F_3 (XVII), was obtained by the oxidation of XIV with OsO_4 followed by Pb(OAc)_4 oxidation. Thus, IV contains a naphthoquinone (IX) and an open chain form of tolypolide F_1. Chemical properties and NMR spin decoupling studies of IV and methoxytolypocyclonone (XVIII) support the structure IV. By the treatment with conc. HCl in methanol, I afforded 1'-O-methyltolypocyclonide (XXII), which can be derived into Va, Vb and XVIII. All the proton signals in the NMR of I can reasonably be accounted for by the proton signals of III and IV. The NMR indicates also that III combines at the C_4 position of IV. On the basi of these findings the structure I is proposed for tolypomycin Y.
天然有機化合物討論会の論文
1968-09-20

3 新抗生物貭Tolypomycinの構造

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