The First Example of the Stereoselective Synthesis of 7β-Carbamoyl-4,5α-epoxymorphinan via a Novel and Reactive γ-Lactone
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概要
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7β-Carbamoyl-4, 5α-epoxymorphinans 5 were stereoselectively synthesized from the 7α-carboxylate intermediate 3 in the presence of 1, 8-diazabicyclo[5.4.0]undec-7-ene (DBU) and amines under reflux conditions in mesitylene via a novel and reactive γ-lactone 7. These were the first examples of the Stereoselective syntheses of 7β-substituted 4, 5α-epoxymorphinans. The mechanism of the reaction process was elucidated as follows : 1) epimerization of 7α-carboxylate 3, 2) intramolecular lactonization of 7β-carboxylate 6, and 3) aminolysis of the resultant γ-lactone 7. The aminolysis of the isolated reactive γ-lactone 7 with allylamine and the alcoholysis with MeOH in the presence of NaBH_4 proceeded at room temperature. The γ-lactone 7 can be a useful intermediate for the preparation of 7β-substituted 4, 5α-epoxymorphinans that would be potent selective δ opioid receptor ligands. The stereoselective syntheses of the 7α-carbamoyl-4, 5α-epoxymorphinans 9 from 7α-carboxylate 3 via 7α-carboxylic acid were also successful.
- 公益社団法人日本薬学会の論文
- 2004-06-01
著者
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Nagase H
Basic Research Laboratories Toray Industries Inc.
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Nagase Hiroshi
Pharmaceutical Research Laboratories Toray Industries Inc.
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北村 和則
富山化学工業株式会社綜合研究所
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FUJII Hideaki
Pharmaceutical Research Laboratories, Toray Industries, Inc.
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HIRANO Noriyuki
Pharmaceutical Research Laboratories, Toray Industries, Inc.
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UCHIRO Hiromi
Pharmaceutical Research Laboratories, Toray Industries, Inc.
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KAWAMURA Kuniaki
Pharmaceutical Research Laboratories, Toray Industries, Inc.
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Fujii Hideaki
Pharmaceutical Research Laboratories Toray Industries Inc.
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Uchiro Hiromi
Pharmaceutical Research Laboratories Toray Industries Inc.
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Uchino H
Department Of Applied Chemistry Faculty Of Science Science University Of Tokyo
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Uchiro Hiromi
Department Of Applied Chemistry Faculty Of Science Science University Of Tokyo
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北村 和則
Kyoto Pharmaceutical University
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Kawamura K
Pharmaceutical Research Laboratories Toray Industries Inc.
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Hirano N
Pharmaceutical Research Laboratories Toray Industries Inc.
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