71 イオノフォアポリエーテル抗生物質リリノマイシンの立体選択的合成

概要

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In connection with our interest in the stereoselective total synthesis of polyether and macrolide antibiotics, we have recently developed a common synthetic approach to these complex compounds using D-glucose as a chiral starting material. We report here total synthesis of salinomycin, the polyether antibiotic produced by streptmyces alubs, known as a potent anticoccidia agent. In our synthetic plan, salinomycin was expected to be synthesized from three segments, A(C1-C9), B(C10-C17), and C(C18-C30). the synthesis of A and B was performed from D-glucose using the method recently established in the synthesis of macrolides. The segment C was synthesized completely stereoselectively from L-ethyl lactate, D-glycelaldehyde and D-glucose. After coupling of B(aldehyde) and C(acetylene), the resulting C10-C30 segment was converted via Lindler's reduction, bisspiroketalization, etc, to the known ethyl ketone(C10-C30), which was the degradation product of salinomycin, and already converted to salinomycin by cross aldol reaction with segment A. Therefore, a highly stereoselective formal total synthesis of salinomycin was thus achieved. An improved total synthesis is now in progress.
天然有機化合物討論会の論文
1986-09-09