81(PA3-1) 新規抗生物質インジソシンの構造決定と合成(ポスター発表の部)

概要

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A new antibiotic indisocin was purified from the culture filtrate of Nocardia blackwellii MG323-hF2 which was isolated from the soil sample collected at Shinagawa-ku, Tokyo, Japan. Indisocin is too unstable to be isolated as the intact substance but stable in ortanic solvents such as methanol and chloroform. The structure was determined by spectroscopic analysis, chemical modification and degradation. The synthesis of its unique partial structure, 1-chloro-1-isocyanovinyl group was accomplished by Wittig-Horner type reaction of carbonyl compounds with diethyl (chloro isocyanomethyl)-phosphonate (7) which was prepared by halogenation of diethyl(isocyanomethyl)phosphonate (6) with butyllithium and tetrachloro-methane. Various 1-chloro-1-isocyanoethenes including indisocin, were synthesized from 7 and the corresponding carbonyl compounds. From the chemical-shifts of olefinic protons in these isocyano compounds, the stereochemistry of olefinic group in indisocin was determined to be E-form by application of Pascual's rule.
天然有機化合物討論会の論文
1987-07-25