Acetogenic isoquinoline alkaloids .96. Circular dichroism of naphthyldihydroisoquinoline alkaloids: Determination of the axial configuration of yaoundamine A

被引：16

作者：

Bringmann, G

Stahl, M

Gulden, KP

机构：

[1] Institut für Organische Chemie, Universität Würzburg, Am Hubland

来源：

TETRAHEDRON | 1997年 / 53卷 / 08期

关键词：

D O I：

10.1016/S0040-4020(97)00049-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The absolute axial configuration of yaoundamine A, a naphthyldihydroisoquinoline alkaloid recently isolated from Ancistrocladus korupensis, was elucidated by comparison of experimental and theoretical Circular Dichroism (CD) spectra. An extensive semiempirical (AM1) analysis of the conformational properties of yaoundamine A and its atropodiastereomer revealed an interesting long-range mutual interaction of the local conformations in the axis and of the dihydroisoquinoline system via the 8-methoxy group as a ''molecular clutch''. Subsequent calculation and Boltzmann-weighting of single-conformation CD spectra (CNDO/2S - C.I.) gave a thermal average CD spectrum matching the experimental one very closely. (C) 1997 Elsevier Science Ltd.

引用

页码：2817 / 2822

页数：6

共 16 条

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