Synthesis of Quinolizine Derivatives. V. Studies on Diastereoisomer of Ethyl 3-Quinolizidinecarboxylate.

スポンサーリンク

概要

• 論文の詳細を見る

• Steric configuration of the two diastereoisomers of ethyl 3-quinolizidinecarboxylate (I) was examined and it was proved from following facts that (Ia) (picrate, m.p. 160〜161°) has the A-type and (Ib) (picrate, m.p. 144〜146°) has the B-type orientation. It was shown that (i) quinolizidine ring is in trans type ; (ii) basic isomerization of (I) and (Ia) afforded a fair amount of (Ib) ; and that (iii) reduction of (Ia) and (Ib) with lithium aluminum hydride resulted in their derivation to 3-lupinine (IIa) and 3-epi-lupinine (IIb), respctively. The steric configuration of (IIa) and (IIb) had previously been approximately determined from measurement of their infrared spectra and dipole moment. It was confirmed through preparation of the tosylates of (IIa) and (IIb), and comparison of their chemical properties that (IIa) had an axial -CH_2OH group and (IIb), the equatorial-CH_2OH.

• 公益社団法人日本薬学会の論文
• 1959-09-20

著者

• 野池 美哉

  Faculty of Pharmaceutical Sciences, University of Tokyo

• 大木 貞雄

  Faculty Of Pharmaceutical Sciences University Of Tokyo

• 野池 美哉

  Faculty Of Pharmaceutical Sciences University Of Tokyo:(present Address)tokyo Research Laboratory Ta

関連論文

• Synthesis of Quinolizine Derivatives. XIII. On the Relationship between Chemical Structure and Uterus Contracting Action of Quinolizidine Derivatives, and Synthesis of Some of these Derivatives.
• Synthesis of Quinolizine Derivatives. IX. Synthesis of 3,3'-Polymethylenediquinolizidine
• Synthesis of Quinolizine Derivatives. V. Studies on Diastereoisomer of Ethyl 3-Quinolizidinecarboxylate.
• Synthesis of Quinolizine Derivatives. IV. : Synthesis of 3-(N'-Methyl-2'-piperidyl)-quinolizidine
• Synthesis of Quinolizine Derivatives. III. : Syntheses of 3-Aminomethyl-and 3-Dimethylaminomethylquinolizidine and dl-3-Lupinine.
• Synthesis of Quinolizine Derivatives. II. : Syntheses of 3-Phenyl- and 3-p-Acetaminophenylquinolizidine.
• ヒノリチン誘導体の合成研究(1)-3-(β-Diethylaminoethyl)-octahydroquinolizineの合成-

スポンサーリンク