Synthesis of C-Nor Emetine Pyman

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概要

• 論文の詳細を見る

• The four stereoisomers of C-nor emetine Pyman (2) were synthesized and isolated as their hydrobromides (2a-d・2HBr). Reduction of 3,11b-trans dehydro C-nor emetine Pyman (13a) gave an inseparable mixture of 2a and 2b. They were converted into the corresponding 2-phenoxybenzoyl amides (14a, b), and the 3,11b-trans C_<1'>-epimers, 14a and 14b, were chromatographically separated. Similarly, the 3,11b-cis C_<1'>-epimers, 14c and 14d, were obtained from cis dehydro C-nor emetine Pyman (13b). The configurations of 14a and 14d were determined by X-ray crystallographic analysis. Reduction of 14a-d with BH_3・SMe_2 complex and hydrogenolysis over Pd-catalyst followed by treatment with HBr-AcOH gave 2a-d・2HBr in good yields.

• 社団法人日本薬学会の論文
• 1992-06-25

著者

• 石田 昭彦

  Organic Chemistry Research Laboratory Tanabe Seiyaku Co. Ltd.

• 武田 幹男

  Organic Chemistry Research Laboratory, Tanabe Seiyaku Co., Ltd.,

• 原田 直之

  Organic Chemistry Research Laboratory, Tanabe Seiyaku Co., Ltd.,

• 岡田 達典

  Organic Chemistry Research Laboratory, Tanabe Seiyaku Co., Ltd.,

• 岡村 公生

  Organic Chemistry Research Laboratory, Tanabe Seiyaku Co., Ltd.,

• 伊達 忠正

  Organic Chemistry Research Laboratory, Tanabe Seiyaku Co., Ltd.,

• 原田 直之

  Lead Optimization Research Laboratory Tanabe Seiyaku Co. Ltd.

• 岡田 達典

  Organic Chemistry Research Laboratory Tanabe Seiyaku Co. Ltd.

• 岡村 公生

  Organic Chemistry Research Laboratory Tanabe Seiyaku Co. Ltd.

• 武田 幹男

  Organic Chemistry Research Laboratory Tanabe Seiyaku Co. Ltd.

• 伊達 忠正

  Organic Chemistry Research Laboratory Tanabe Seiyaku Co. Ltd.

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