Synthetic Studies on Spiroketal Natural Products. II. An Enantioselective Synthesis of (R)- and (S)-1,7-Dioxaspiro[5.5]undecane

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概要

• 論文の詳細を見る

• Both enantiomers of 1,7-dioxaspiro[5.5]undecane, a chiral compound with C_2 symmetry, were stereoselectively synthesized from an (R)-sulfoxide compound 8. The reaction of menthyl (S)-p-toluenesulfinate with a Grignard reagent gave the chiral sulfoxide (8), which was derived to a dihydropyran (12) by a several-step sequence. The base-catalyzed intramolecular Michael reaction of 12 exclusively afforded a dioxaspiro product (13) as a single stereoisomer. An acidic treatment of 13 resulted in isomerization of the spiro center to give 14. Desulfurization of 13 and 14 over Raney nickel in the presence of sodium hydroxide gave (R) -and (S)-1,7-dioxaspiro[5.5]undecane (R-1 and S-1), respectively.

• 社団法人日本薬学会の論文
• 1988-09-25

著者

• 今西 武

  Faculty Of Pharmaceutical Sciences Osaka University

• 岩田 宙造

  Faculty of Pharmaceutical Sciences, Osaka University

• 服部 浩二

  Faculty Of Pharmaceutical Sciences Osaka University

• 藤田 昌宏

  Faculty of Pharmaceutical Sciences, Osaka University

• 黒木 俊夫

  Faculty of Pharmaceutical Sciences, Osaka University

• 内田 秀治

  Faculty of Pharmaceutical Sciences, Osaka University

• 岩田 宙造

  大阪大学薬学部製薬化学科

• 岩田 宙造

  Faculty Of Pharmaceutical Sciences Osaka University

• 藤田 昌宏

  Exploratory Research Laboratories Dainippon Pharmaceutical Company Ltd.

• 内田 秀治

  Faculty Of Pharmaceutical Sciences Osaka University

• 黒木 俊夫

  Fuji-gotemba Research Laboratories Chugai Pharmaceutical Company Ltd.

• Fujita M

  Univ. Tokyo

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