Syntheses of 6-Amino-1,2-dihydroxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-5-ol Derivatives

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概要

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• Investigations on the essential conformation of adrenergic catecholamines led us to synthesize 6-amino-1,2-dihydroxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-5-ol derivatives (1), which are seven-membered rigid analogues of catecholamines. Although catalytic reduction of the amino ketones (9 and 10) leading to the analogues of noradrenaline and isoproterenol (1a and 1c) yielded mixtures of 5,6-cis and trans isomers, it was found that lithium aluminum hydride reduction of α-hydroxyimino ketone (12) gave exclusively cis-amino alcohol (13a-cis) and that reduction of α-acetamido ketone (14) with sodium borohydride followed by hydrolysis afforded 13a-trans. Several pairs of 5,6-cis and trans isomers of 1 were prepared by catalytic reduction of 13a-cis and 13a-trans or their Nsubstituted derivatives. N-tert-Butyl derivative (1d-trans) was prepared via 13d-trans which was obtained by hydrolysis of an azirizino compound (24).

• 公益社団法人日本薬学会の論文
• 1978-02-25

著者

• 伊藤 克己

  Pharmaceutical Research Laboratories Iii Pharmaceutical Research Division Takeda Chemical Industries

• 杉原 弘貞

  Central Research Division, Takeda Chemical Industries, Ltd.,

• 伊藤 克巳

  Central Research Division, Takeda Chemical Industries, Ltd.,

• 岡 良和

  Central Research Division, Takeda Chemical Industries, Ltd.

• 伊藤 克巳

  武田薬品工業

• 伊藤 克已

  Central Research Division Takeda Chemical Industries Ltd.

• 三宅 昭夫

  Central Research Division, Takeda Chemical Industries, Ltd.

• 多田 憲生

  Central Research Division, Takeda Chemical Industries, Ltd.

• 多田 憲生

  Central Research Division Takeda Chemical Industries Ltd.

• 岡 良和

  Chemistry Laboratories Central Research Division Takeda Chemical Industries Ltd.

• 三宅 昭夫

  Chemistry Laboratories Central Research Division Takeda Chemical Industries Ltd.

• 三宅 昭夫

  Central Research Division Takeda Chemical Industries Ltd.

• 杉原 弘貞

  Pharamaceutical Research Laboratories I Pharmaceutical Research Division Takeda Chemical Industries

• 杉原 弘貞

  Central Research Division Takeda Chemical Industries. Ltd.

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