Stereochemical studies on ascaulitoxin:: a J-based NMR configurational analysis of a nitrogen substituted system

被引：29

作者：

Bassarello, C

Bifulco, G

Evidente, A

Riccio, R

Gomez-Paloma, L

机构：

[1] Univ Salerno, Dipartimento Sci Farmaceut, I-84084 Fisciano, SA, Italy

[2] Univ Naples Federico II, Dipartimento Sci Chim Agr, I-80055 Portici, NA, Italy

来源：

TETRAHEDRON LETTERS | 2001年 / 42卷 / 49期

关键词：

heteronuclear coupling constants; phytotoxins; bioherbicides; ascaulitoxin; relative stereochemistry;

D O I：

10.1016/S0040-4039(01)01815-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The J-based NMR configurational analysis was applied to the determination of relative stereochemistry of the ascaulitoxin molecule (1), a phytotoxic metabolite with herbicidal activity against Chenopodium album. This method is particularly suitable for acyclic structures containing hydroxy(alkoxy) groups, because in this kind of system, besides (3)J(H-H) and (3)J(C-H), (2)J(C-H) values can also be used to extract additional angular information. Ascaulitoxin (1), with its bis-amino acid side chain containing four stereocenters, two of which with nitrogen substituents, required a more careful analysis of heteronuclear J-couplings, also in comparison with theoretical values obtained by ab initio methods. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：8611 / 8613

页数：3

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