NMR determination of the absolute configuration of an α-exo-methylene-γ-lactone

被引：7
|
作者：
Fukui, H
Fukushi, Y [1 ]
Tahara, S
机构：
[1] Hokkaido Univ, Grad Sch Agr, Div Appl Biosci, Kita Ku, Sapporo, Hokkaido 0608589, Japan
[2] Japan Sci & Technol Corp, CREST, Kawaguchi, Saitama 3320012, Japan
来源：
BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY | 2000年 / 64卷 / 07期
关键词：
igalan; alpha-exo-methylene-gamma-lactone; NOE; absolute configuration; MBCC;
D O I：
10.1271/bbb.64.1345
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：
Both the enantiomers of the axially chiral reagent, 2'-methoxy-1,1'-binaphthalene-2-carbohydroximoyl chloride (MBCC), were used to convert igalan, an alpha-exo-methylene-gamma-lactone, to yield 4,5-dihydroisoxazoles. The absolute configuration of igalan was determined to be (3aR,5R,6R,7aR)-6-ethenylhexahydro-6-methyl-3-methylene-5-(1-methylethenyl)-2(3H)-benzofuranone (IUPAC name) on the basis of NOE correlations in these derivatives. The absolute configurations of other alpha-exo-methylene-gamma-lactones can be determined by the same method.
引用
收藏
页码：1345 / 1351
页数：7
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