56 ピロリジジンアルカロイドの簡便な新合成法

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概要

• 論文の詳細を見る

• One-pot synthesis of pyrrolizidine skeleton has been achieved by 1,3-dipolar cycloaddition of olefines to intermediary N-trimethyl-silylmethyl-1-pyrrolinium salt derived from trimer of 1-pyrroline (1). This reaction has provided simple synthesis of pyrrolizidine alkaloids. Reaction of 1 with trimethylsilylmethyl trifluoromethanesulfonate and methyl acrylate in the presence of cesium fluoride in DME gave methyl pyrrolizidine-1-carboxylate (3). The product, 3 was converted into (±)-trachelanthamidine (4) by reduction with lithium aluminum hydride. By the procedure similar to the former reaction, 1 reacted with ethyl 2-chloroacrylate to give ethyl 1,2-didehydro-pyrrolizidine-1-carboxylate (7), of which physical and spectral data were consistent with an authentic specimen synthesized from ethyl pyrrolizidine-1-carboxylate (8) through phenylselenylation. Compound, 7 has been known as a precursor of (±)-supinidine and (±)-isoretronecanol.

• 天然有機化合物討論会の論文
• 1981-09-10

著者

• 今井 信行

  Shizuoka College Of Pharmacy

• 関屋 実

  School Of Pharmaceutical Sciences University Of Shizuoka

• 寺尾 良保

  School Of Pharmaceutical Sciences University Of Shizuoka

• 寺尾 良保

  静岡薬大

• 今井 信行

  静岡薬大

• 阿知波 一雄

  静岡薬大

• 関屋 実

  静岡薬大

関連論文

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• Thermal Rearrangements of Allyl 2,2-Dichloro-, 1,2-Dichloro- and 1,2,2-Trichloro-substituted Vinyl Sulfides
• Novel Rearrangements of α-N-Alkylamido-substituted Sulfides and Sulfones
• Syntheses and Reactions of Phenylthio-and Propylthioacetylenic Compounds
• Enantioface-Differentiating Epoxidation of Alkylidenemalononitriles with Molecular Oxygen, catalyzed by Chiral Tertiary Amines
• Formic Acid Reduction. XXVIII. Kinetic Studies on the Formic Acid Reduction of 1,1'-Benzylidenedipiperidine
• A New Insertion Reaction of Diazoalkanes with Dialkylaminomethyl Esters of Dialkyldithiocarbamic Acid and of Ethylxanthic Acid
• Chlorinolyses of Alkyl (or Aryl) Phthalimidomethyl Sulfoxides with Sulfuryl Chloride, Chlorine and Thionyl Chloride
• Nucleophilic Substitution of Alkyl (or Aryl) Imidomethyl Sulfones. A New Convenient Synthesis of Alkane (or Arene) sulfinates
• Decarboxylation Reaction. VIII. Reaction of Electron-deficient Carbon-Carbon Double Bonds with Trichloroacetic Acid. A Unique 1,1-Dichlorocyclopropane Formation through β-Trichloromethylation
• Formic Acid Reduction. XXVI. α, β-Reduction of Conjugated Nitriles with Formic Acid
• Decarboxylation Reactions. V. Reaction of N-Benzylideneanilines with Propiolic Acid
• Formic Acid Reduction. XXIV. Path of the Reductive Fission of the Centered β-Carbon Bond of Alkylidenebisketones
• Formic Acid Reduction. XXIII. Kinetic Studies on the Formic Acid Reduction of Carbon-Carbon Double Bond Adjacent to Carbonyl
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• オクテット
• 1,3-Dipolar Cycloaddition Leading to N-Acylated Pyrrolidines and 2,5-Dihydropyrroles
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• 56 ピロリジジンアルカロイドの簡便な新合成法
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• 鵜飼貞二先生を悼む
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• 「速報をどう考える」のパネルを読んで : その2
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• トリクロロ酢酸イオンの脱酸素を含むトリクロロ酢酸およびその無水物の反応
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• ケイ素原子の特性を利用する環状付加反応
• Alkylation of Phthalimidines
• Synthesis of N-(Alkylaminomethyl) amides

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