Synthetic Studies on Lythraceae Alkaloids. II. The Mannich Reaction of Isopelletierine with 3-Methoxybenzaldehyde and 3-Hydroxybenzaldehyde

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概要

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• The Mannich reaction of isopelletierine (III) with 3-methoxybenzaldehyde (VI) in aqueous sodium hydroxide afforded the trans- and cis-quinolizidine (VIII and IX) in the 1 : 6 ratio, whereas the reaction with 3-hydroxybenzaldehyde (VII) gave almost exclusively the trans-quinolizidine (X). On the other hand, the reaction with VI in methanol afforded VIII and IX in the 6 : 1 ratio. On the basis of the detailed experiments the Mannich reaction of III with arylaldehyde under an alkaline condition was found to afford at first cis-4-arylquinolizidin-2-one, which then isomerized into the corresponding trans-isomer. And the stereoselectivity of this reaction was found to depend on solvents, solubilities of the starting arylaldehydes and products, and reaction times.

• 社団法人日本薬学会の論文
• 1975-07-25

著者

• 小川 信男

  Faculty Of Pharmaceutical Sciences Kanazawa University

• 荒田 義雄

  Faculty Of Pharmaceutical Sciences Kanazawa University

• 花岡 美代次

  Faculty of Pharmaceutical Sciences, Kanazawa University

• 花岡 美代次

  金沢大学薬学部

• 花岡 美代次

  Faculty Of Pharmaceutical Sciences Osaka University

• 花岡 美代次

  Faculty Of Pharmaceutical Sciences Kanazawa University

• 清水 憲治

  Faculty of Pharmaceutical Sciences, Kanazawa University

• 清水 憲治

  Faculty Of Pharmaceutical Sciences Kanazawa University

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