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

页码：1345 / 1351

页数：7

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