P-46 海洋産ポリエーテルマクロリド、ハリコンドリンBの全合成研究(ポスター発表の部)

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概要

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• Halichondrins are a class of polyether macrolides isolated from the marine sponge Halichondria okadai Kadota in low yield. Halichondrin B (1) is a remarkably effective antitumor agent in vitro andin vivo. However, this marine polyether macrolide is not readily available from its natural source. Additionally, 1 is a considerably complex molecule containing 32 asymmetric carbons, substituted tetrahydrofuran and pyran and spiroketal rings, and a large membered lactone. Among many synthetic efforts toward 1, Kishi's group succeeded in the first total synthesis of 1 in 1992. For the purpose of establishing a stereoselective and efficient synthetic pathway of 1, we begun to synthesize 1 in 1989. We report here highly stereocontrolled syntheses of the polyether portion (33) and macrolide portion (31). As our synthetic outline was shown in scheme 1, halichondrin B (1) was expected to be synthesized from four convenient fragments, 2, 3, 5 and 6. Highly Stereocontrolled syntheses of these four fragments have accomplished. The macrolide portion (31) of 1 was synthesized by lactonization of the seco acid (30), derived from 2, 3 and 5, using the modified Yamaguchi's method. On the other hand, the polyether portion (33) was also synthesized from 32, derived from 5, and 6. Other coupling programs toward the total synthesis of 1 is now in progress.

• 天然有機化合物討論会の論文
• 1994-09-20

著者

• 米光 宰

  岡山理大理

• 米光 宰

  Faculty of Pharmaceutical Sciences, Hokkaido University

• 米光 宰

  Faculty Of Pharmaceutical Sciences Hokkaido University

• 堀田 清

  北大薬

• 長澤 正明

  北大薬

• 八谷 俊一郎

  北大薬

• 荻原 和仁

  北大薬

• 八谷 俊一郎

  Faculty of Pharmaceutical Sciences, Hokkaido University

• 長澤 正明

  Faculty of Pharmaceutical Sciences, Hokkaido University

• 八谷 俊一郎

  Faculty Of Pharmaceutical Sciences Hokkaido University

• 堀田 清

  Faculty Of Pharmaceutical Sciences Health Science University Of Hokkaido

• 長澤 正明

  Faculty Of Pharmaceutical Sciences Hokkaido University

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