80 糖質Synthonを用いる生理活性天然物の合成 : 抗生物質A23187の合成研究 IV

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Previously we reported the transformation of D-glucose into two synyhons for antibiotic A23187 (1). Synthesis of dioxaspiro unit Synthon (2) was coupled with another synthon (3) by the use of t-BuLi in n-hexane-HMPA mixture at ?-30℃. After replacement of silyl group in (9) by benzoyl group, thioketal in (11) was removed to generate ketone (12). Heating of (12) in 10% aqH_3PO_4-THF afforded a dioxaspiro-compound (13). Introduction of benzoxazole unit Carboxylic acid (26), prepared from (13) in 4 steps, was condensed with aminophenol (17) via mixed anhydride to give benzoxazole derivative (27). Introduction of pyrrole unit Pyrrole Grignard reagent reacted with benzenethiol or benzeneselenol ester in the presence of CuI to give 2-acylpyrrole. Application of this reaction for the synthesis of target compound (1) is under investigation.
天然有機化合物討論会の論文
1981-09-10