Synthetic Studies on Spiroketal Natural Products. IV.A Stereoselective Synthesis of (3S, 5S, 6R, 9R, R_S)-3-Benzyloxymethyl-9-hydroxymethyl-5-(p-tolyl)sulfinyl-1,7-dioxaspiro[5.5]undecane, a Key Intermediate for Talaromycins

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概要

• 論文の詳細を見る

• A dioxaspiro compound (4), a common intermediate for the synthesis of talaromycin A (1) and (-)-talaromycin B (2), was synthesized by two routes utilizing two kinds of asymmetric recognition of prochiral 1,3-diols controlled by sulfinyl chirality, that is, firstly by acid promoted diastereoselective C-O bond fission of the bicyclic acetal (7) to give the dihydropyran derivative (6), which has an S-hydroxymethyl group at the C3-position (7→6), and secondly by diastereoselective intramolecular Michael addition of the diol (5), in which the three chiral centers at C5,C6,C9 were constructed in one step (5→4).

• 社団法人日本薬学会の論文
• 1993-02-15

著者

• 今西 武

  Faculty Of Pharmaceutical Sciences Osaka University

• 竹本 佳司

  Faculty Of Pharmaceutical Sciences Osaka University

• 田中 徹明

  Faculty of Pharmaceutical Sciences, Osaka University

• 岩田 宙造

  Faculty of Pharmaceutical Sciences, Osaka University

• 前崎 直容

  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

• 盛谷 恭典

  Faculty of Pharmaceutical Sciences, Osaka University

• 今西 武

  大阪大学大学院薬学研究科

• 岩田 宙造

  阪大院薬

• 前崎 直容

  阪大院薬

• 田中 徹明

  阪大院薬

• 田中 徹明

  Faculty Of Pharmaceutical Sciences Osaka University

• Tanaka T

  Kvushu Univ. Fukuoka Jpn

• Tanaka T

  Osaka Univ. Osaka Jpn

• Takemoto Yoshiji

  Faculty Of Pharmaceutical Sciences Osaka University

• Takemoto Y

  Graduate School Of Pharmaceutical Sciences Kyoto University

• 岩田 宙造

  Faculty Of Pharmaceutical Sciences Osaka University

• 藤田 昌宏

  Exploratory Research Laboratories Dainippon Pharmaceutical Company Ltd.

• Tanaka Tetsuaki

  Faculty Of Pharmaceutical Sciences Osaka University

• 盛谷 恭典

  Faculty Of Pharmaceutical Sciences Osaka University

• Imanishi Takeshi

  Graduate Shool Of Pharmaceutical Sciences Osaka University

• Imamura T

  Faculty Of Pharmaceutical Sciences Osaka University

• Fujita M

  Univ. Tokyo

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