25 ポリエーテル抗生物質リソセリンの立体選択的全合成(口頭発表の部)

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• The polyether antibiotics, well known as the ionophore, have provided a widespread field for organic chemists because of their complex structures and biologically important properties. In connection with our interest in establishing a common synthetic methodology of the polyether antibiotics, we chose four representative polyether antibiotics, lysocellin (1), salinomycin (2), lasalocid A (3), and isolasalocid A (4), as the synthetic targets. Syntheses of three compounds, 2, 3, and 4 have already finished. We describe herein the stereocontrolled total synthesis of lysocellin (1), remained final target molecule. Lysocellin (1), isolated from Streptomyces cacaoi var asoensis in 1975, is the first and representative member of the lysocellin family. The relative and absolute configuration was determined by X-ray crystallography of the silver salt. Lysocellin (1) was retrosynthetically divided into three convenient fragments, C1〜C9 fragment (6), C11〜C15 fragment (9) and C16〜C23 fragment (10) respectively. Two fragments 6 and 9 were stereoselectively prepared from D-glucose. On the other hand, 10 was also stereoselectively synthesized from the β-ketophosphonate (21) and the aldehyde (22), derived from D-mannitol, using the stereocontrolled Michael reaction with Me_2CuLi and the Grignard reaction to the α, β-unsaturated ketone (23). After coupling 9 onto 10, 28 was converted into the triol (37) via 34 and 35. PCC oxidation of 37 and the, subsequent acid treatment of 38 stereoselectively afforded the γ-lactol derivative (38a). Finally, the zinc enolate of the ethylketone (7) was coupled with the aldehyde (6) to give the lysocellin (1), whose sodium salt was identical, in terms of its melting point, optical rotation and spectral data (^1H NMR and IR), with the natural product.

• 天然有機化合物討論会の論文
• 1992-09-10

著者

• 米光 宰

  岡山理大理

• 米光 宰

  Faculty of Pharmaceutical Sciences, Hokkaido University

• 米光 宰

  北大薬

• 米光 宰

  Faculty Of Pharmaceutical Sciences Hokkaido University

• 田中 和宏

  Faculty Of Pharmaceutical Sciences Hokkaido University

• 堀田 清

  北大薬

• 井上 隆行

  北大薬

• 田中 和宏

  北大薬

• 堀田 清

  Faculty Of Pharmaceutical Sciences Health Science University Of Hokkaido

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