DEUTERIUM LABELING OF ENT-KAUR-16-EN-19-OIC ACID AT CARBON-6 AND CARBON-7

被引:16
作者
CASTELLARO, SJ
DOLAN, SC
MACMILLAN, J
WILLIS, CL
机构
[1] School of Chemistry, The University of Bristol, Bristol
关键词
Deuterium labelling; gibberellin; kaura-6,16-dienoic acid; kaurenoic acid; kaurenolide; synthesis; stereospecificity;
D O I
10.1016/0031-9422(90)85023-9
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
[6α-2H]-, [6β-2H]-, [7α-2H]-, [7β-2H]-, [6,6-2H2]-, [7,7-2H2]- and [6β,7β-2H2]ent-Kaur-16-en-19-oic acids have been prepared from 7β-hydroxykaurenolide, a metabolite of the fungus, Gibberella fujikuroi. The chemical and stereochemical purity of the labelled acids have been determined by GC-MS and by 1H and 2H NMR spectroscopy. ent-[7-2H]Kaura-6,16-dienoic acid and methyl ent-[6-2H]-17-hydroxykauran-6-en-19-oate have also been prepared. Their 1H NMR spectra show that a previous assignment of the 6- and 7-hydrogen signals in ent-kaura- 6,16-dienoic acid should be reversed. © 1982.
引用
收藏
页码:1823 / 1831
页数:9
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