Synthesis of Fluorine Analogues of Vitamin E. II. : Synthesis of 2-(3-Chloropropyl)-2,5,7,8-tetramethyl-6-chromanol and Its Application for Stereocontrolled Witting Reaction with Trifluoromethyl Ketones

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概要

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• As the extension of our research to find a biologically active analogue of vitamin E, a more convenient method for the synthesis of fluorine derivatives of 6-chromanol than our previous method was developed. Thus, 2-(3-chloropropyl)-2,5,7,8-tetramethyl-6-chromanol (3) was synthesized by the reaction of 6-chloro-3-methyl-2-hexen-1-ol (2) and trimethylhydroquinone, and the phosphonium ylides (5 and 6) derived from 3 were condensed with trifluoromethylated ketones to give 2-(trifluoroprenyl)-6-chromanol compounds (1a, 1b and 1c) by means of the Wittig reaction as modified by Schlosser. By the use of this revised procedure, the total yields of the chromanols were much improved. Further, the modified Wittig reaction showed higher stereoselectivity than the previous syntheses of these compounds. The double bonds of the side-chain of the products were reduced to give fluorine derivatives of tocopherol analogues. Compound 3 was found to be a useful intermediate for the facile synthesis of vitamin E derivatives.

• 社団法人日本薬学会の論文
• 1988-08-25

著者

• 三木 卓一

  Department of Toxicology, Faculty of Pharmaceutical Sciences, Setsunan University

• 熊懐 稜丸

  摂南大・薬

• 永井 隆文

  Faculty Of Pharmaceutical Sciences Setsunan University

• 小山 まゆみ

  Faculty of Pharmaceutical Sciences, Setsunan University

• 安藤 章

  Faculty of Pharmaceutical Sciences, Setsunan University

• 三木 卓一

  Faculty of Pharmaceutical Sciences, Setsunan University

• 熊懐 稜丸

  Faculty of Pharmaceutical Sciences, Setsunan University

• 田村 美穂子

  Faculty of Pharmaceutical Sciences, Setsunan University

• Ando A

  Faculty Of Pharmaceutical Sciences Setsunan University

• 熊懐 稜丸

  摂南大薬

• 熊懐 稜丸

  Faculty Of Pharmaceutical Sciences Setsunan University

• 熊懐 稜丸

  Faculty Of Pharmaceutical Sciences Kyushu University:(present Address)tokyo College Of Pharmacy Kash

• 田村 美穂子

  Faculty Of Pharmaceutical Sciences Setsunan University

• 三木 卓一

  Department Of Toxicology Faculty Of Pharmaceutical Sciences Setsunan University

• 三木 卓一

  武田薬品工業株式会社研究開発本部

• 小山 まゆみ

  Faculty Of Pharmaceutical Sciences Setsunan University

• Miki Takuichi

  Department Of Toxicology Faculty Of Pharmaceutical Sciences Setsunan University

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