A stereostructural study of 17-hydroxylupanine and its perchlorate

被引：8

作者：

Thiel, J ^{[1
]}

Boczon, W ^{[1
]}

Wysocka, W ^{[1
]}

机构：

[1] Adam Mickiewicz Univ, Fac Chem, PL-60780 Poznan, Poland

来源：

MONATSHEFTE FUR CHEMIE | 2000年 / 131卷 / 10期

关键词：

bisquinolizidine alkaloids; configuration; conformation; NMR spectroscopy; DDQ oxidation;

D O I：

10.1007/s007060070040

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The bisquinolizidine carbinolamine 17-hydroxylupanine was synthesized de novo from lupanine using 2,3-dichloro-5,6-dicyano-1,4-benzoquinone; its structure was established by NMR techniques. The equatorial position of the hydroxy group as well as the prevailing boat form of ring C were determined. As expected, the carbinolamine converted into the C17=N16 anhydronium perchlorate upon treatment with HClO4. NMR analysis of the salt revealed a conformational equilibrium within rings A and D, whereas rings B and C remain rigid.

引用

页码：1073 / 1081

页数：9

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