Preparation of cruciferous phytoalexin related metabolites, (-)-dioxibrassinin and (-)-3-cyanomethyl-3-hydroxyoxindole, and determination of their absolute configurations by vibrational circular dichroism (VCD)

被引：35

作者：

Monde, K ^{[1
]}

Taniguchi, T

Miura, N

Nishimura, SI

Harada, N

Dukor, RK

Nafie, LA

机构：

[1] Hokkaido Univ, Grad Sch Sci, Frontier Res Ctr Postgenom Sci & Technol, Div Biol Sci,Lab Biomacromol Chem,Kita Ku, Sapporo, Hokkaido 0010021, Japan

[2] Japan Bioind Assoc, Sapporo Lab Glycocluster Project, Sapporo, Hokkaido 0010021, Japan

[3] Tohoku Univ, Inst Multidisciplinary Res Adv Mat, Sendai, Miyagi 9808577, Japan

[4] BioTools Inc, Wauconda, IL 60084 USA

[5] Syracuse Univ, Dept Chem, Syracuse, NY 13244 USA

来源：

TETRAHEDRON LETTERS | 2003年 / 44卷 / 32期

关键词：

VCD; dioxindole; dioxibrassinin; phytoalexin; tertiary alcohol;

D O I：

10.1016/S0040-4039(03)01513-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Cruciferous phytoalexin related metabolites, (-)-dioxibrassinin (1) and (-)-3-cyanomethyl-3-hydroxyoxindole (2) were prepared from isatin as racemates and were resolved by chiral HPLC. Their absolute configurations were determined by the new chiroptical technique, vibrational circular dichroism (VCD), as well as by the conventional electronic circular dichroism (ECD). It is concluded that the absolute configurations of the naturally occurring (-)-1 and (-)-2 are both S. (C) 2003 Elsevier Ltd. All rights reserved.

引用

页码：6017 / 6020

页数：4

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