70 1,3-ポリオールの立体構造決定法の開発と関連天然物の合成 : ペンタマイシンの立体構造(口頭発表の部)

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概要

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• The polyene macrolide antibiotics have attracted much attention for their potent antifungal activity and unique structure. The characteristic structural feature of the antibiotics is that they involve 1,3-polyol and all-trans-polyene moieties. However, in most cases even a relative configuration of these 1,3-polyols remains unknown. Convergent synthesis of 1,3-polyols: We have already reported a stereoselective and stepwise method for the synthesis of 1,3-syn and anti-polyols. Recently, an effective and stereocontrolled convergent method for the synthesis of 1,3-polyols has been developed in this laboratory. Using this new method, the first total syntheses of two natural products 3 and 4 having 1,3-synpolyol moiety have been accomplished. Determination of the stereostructure of 1,3-polyols: We have recently developed a reliable strategy for determining the relative and absolute configuration of 1,3-polyols based on the structurespecific ^1H NMR splitting patterns observed in lactones B and C. Based on this new method, the absolute configuration of pantamycin, a polyene macrolide antibiotic, has been determined as shown in structure 51. Furthermore, fungichromin, lagosin, and cogomycin were proved to be the same compound as pentamycin. Thus, their absolute stereostructures should also be shown as 51.

• 天然有機化合物討論会の論文
• 1988-09-26

著者

• 中田 忠

  理研

• 大石 武

  理研

• 大石 武

  Faculty Of Engineering Yokohama National University:(present Address)meiji College Of Pharmacy

• 大石 武

  理研:(現)明治薬科大学

• 中田 忠

  東京理大・理

• 畑 憲明

  理研

• 末永 俊朗

  理研

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