Synthetic Studies on Spiroketal Natural Producys. III. : Enantioselective Synthesis of 1,6-Dioxaspiro[4.5]decane Compounds

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概要

• 論文の詳細を見る

• Two enantiomers of 1,6-dioxaspiro[4.5]decane (1) and all four stereisomers of 2-methyl-1,6-dioxaspiro[4.5]decane (an insect pheromone) (9) were successfully synthesized via a crucial step, an asymmetric five-membered ring cyclization induced by sulfinyl chirality.The alcohol (6), prepared from the optically active sulfoxide (2), were treated with potassium hydride to give spiroketal (7), which was transformed into the isomer (8) by acid. Reductive desulfurization of these products furnished R-1 and S-1,respectively.The ketone (10), also prepared from 2,was reduced with diisobutylaluminum hydride (DIBAL) or DIBAL-ZnCl_2 to afford selectively 15a or 15b, respectively. Base-catalyzed cyclization gave 21a and 21b, which were convertible to 22a and 22b under acidic conditions. The four isomers (21a, 21b, 22a, and 22b) were efficiently transformed into 9a, 9b, 9c, and 9d by removal of the chiral auxiliary.

• 公益社団法人日本薬学会の論文
• 1988-12-25

著者

• 今西 武

  Faculty Of Pharmaceutical Sciences Osaka University

• 岩田 宙造

  Faculty of Pharmaceutical Sciences, Osaka University

• 盛谷 恭典

  Faculty of Pharmaceutical Sciences, Osaka University

• 黒木 俊夫

  Faculty of Pharmaceutical Sciences, Osaka University

• 岩田 宙造

  阪大院薬

• 杉山 憲司

  Faculty Of Pharmaceutical Sciences Osaka University

• 岩田 宙造

  Faculty Of Pharmaceutical Sciences Osaka University

• 井崎 仁史

  Faculty of Pharmaceutical Sciences, Osaka University

• 盛谷 恭典

  Faculty Of Pharmaceutical Sciences Osaka University

• 井崎 仁史

  Faculty Of Pharmaceutical Sciences Osaka University

• 黒木 俊夫

  Fuji-gotemba Research Laboratories Chugai Pharmaceutical Company Ltd.

• Imamura T

  Faculty Of Pharmaceutical Sciences Osaka University

• Kubo S

  Department Of Pharmacology Niigata College Of Pharmacy

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