Chemistry of Tetrahydro-1,3-oxazin-2-one : New Method for the Synthesis of Indoloquinolizidine Derivatives

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概要

• 論文の詳細を見る

• The aldol condensation of the N-Boc-tetrahydro-β-carboline-1-acetate (4) with acrolein in the presence of lithium diisopropylamide (LDA) gave an allyl alcohol (6), which was then treated with methanesulfonyl chloride and triethylamine to give a mixture of the mesylate (8) (55%) and the indolopyrido-3,5-oxyazin-4-one (10) (14%). When 8 was treated with 1,8-diazabicyclo[5.4.0.]-7-undecene (DBU) in dimethylsulfoxide (DMSO) at room temperature, the azetopyridoindoles (12 and 13) were obtained unexpectedly. Alternative preparation of the indolopyrido-3,5-oxazin-4-ones (15 and 16), which are stereoisomers of 10,from 6 followed by heating with DBU in DMSO gave several indoloquinolizidines (18,19 and 20), which are key intermediates for the synthesis of the indole alkaloids vindolosine and vindoline.

• 公益社団法人日本薬学会の論文
• 1991-12-25

著者

• 大石 宏文

  Osaka University of Pharmaceutical Sciences

• 春沢 信哉

  Osaka University of Pharmaceutical Sciences

• 栗原 拓史

  Osaka University of Pharmaceutical Sciences

• 米田 龍司

  Osaka University of Pharmaceutical Sciences

• 栗原 拓史

  大阪薬科大学

• 寒川 愉美

  Osaka University of Pharmaceutical Sciences

• 横出 佳代

  Osaka University of Pharmaceutical Sciences

• Ohishi H

  Osaka University Of Pharmaceutical Sciences

• Ohishi H

  Osaka Univ. Pharmaceutical Sci. Osaka Jpn

• 米田 龍司

  Agroscience Research Laboratories Sankyo Co. Ltd.

• 栗原 拓史

  Osaka College Of Pharmacy

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