CONFORMATIONAL CONSIDERATIONS IN 1-OXAQUINOLIZIDINES RELATED TO THE XESTOSPONGIN/ARAGUSPONGINE FAMILY - REASSIGNMENT OF STEREOSTRUCTURES FOR ARAGUSPONGINE-B AND ARAGUSPONGINE-E

被引：16

作者：

HOYE, TR

NORTH, JT

YAO, LJ

机构：

[1] Department of Chemistry, University of Minnesota, Minneapolis

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1994年 / 59卷 / 23期

关键词：

D O I：

10.1021/jo00102a012

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Conformational aspects of the 1-oxaquinolizidine ring system found in the xestospongin/araguspongine family of natural products has been studied by molecular modeling and NMR spectroscopy. Stereochemical complexities [e.g., (i) cis- vs trans-decalin-like conformers and (ii) relative configuration of variously substituted 1-oxaquinolizidines] associated with this bridgehead nitrogen-containing skeleton are discussed. Experimental equilibrium values are rationalized. Reassignment of the stereostructures for araguspongines B (from 4 to 6) and E (from 5 to 2) is made in light of the above.

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页码：6904 / 6910

页数：7

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