Studies on Tertiary Amine Oxides. LIX. A New Total Synthesis of dl-Allomatridine

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概要

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• 1,1-Ethylenedioxy-9-(2-pyridyl) quinolizidine (1) was converted to N-ethoxycarbonylpyridinium salt (3) via monohydrobromide (2) by successive treatment with ammonium bromide and ethyl bromoacetate. The reaction of 3 with hydrochloric acid was markedly affected with the concentration of the acid. Thus, when 3 was heated with 15-20% hydrochloric acid, ring closure took place accompanied by hydrolysis of the ketal and ester groups and also decarboxylation to give 17-hydroxy compound (4). Heating with triethylamine gave dehydrated pyridinium salt (5) which was reduced with sodium borohydride and then catalytically to dl-allomatridine (6). On the other hand, heating 3 with 5-10% hydrochloric acid gave a carboxylic acid (9) which was also transformed into 6 through an ester (10) and a ring closure product (11) as shown in Chart 2. The action of 30% acid on 3 followed by the similar treatments afforded 1-hydroxy-9-(2-pyridyl) quinolizidine (7). Transformation of 1 to 17-hydroxyallomatridine (8) was further achieved successively by hydrolysis to 1-oxo compound (12), formation of its cyanohydrin (13) and hydrogenation over Raney nickel.

• 公益社団法人日本薬学会の論文
• 1977-01-25

著者

• 盛中 泰洋

  Faculty Of Pharmaceutical Sciences Kyushu University

• 佐伯 清太郎

  Faculty Of Pharmaceutical Sciences Kyushu University

• 浜名 政和

  Faculty Of Pharmaceutical Sciences Kyushu University

• 山下 絢子

  Faculty of Pharmaceutical Sciences, Kyushu University

• 山下 絢子

  Faculty Of Pharmaceutical Sciences Kyushu University

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