STEREOCHEMISTRY OF 14-HYDROXY-BETA-CARYOPHYLLENE AND RELATED-COMPOUNDS

被引：54

作者：

BARRERO, AF ^{[1
]}

MOLINA, J ^{[1
]}

OLTRA, JE ^{[1
]}

ALTAREJOS, J ^{[1
]}

BARRAGAN, A ^{[1
]}

LARA, A ^{[1
]}

SEGURA, M ^{[1
]}

机构：

[1] UNIV JAEN,FAC CIENCIAS EXPTL,DEPT QUIM INORGAN & ORGAN,E-23071 JAEN,SPAIN

来源：

TETRAHEDRON | 1995年 / 51卷 / 13期

关键词：

D O I：

10.1016/0040-4020(95)00104-G

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The isomerization of beta-caryophyllene (3), under treatment with SeO2, is described. Chemical correlations, between 3 and 14-hydroxy-beta-caryophyllene (6) from Juniperus oxycedrus, are established. High resolution H-1 NMR spectra and analysis by molecular mechanics of 3, 6 and 14-acetoxy-beta-taryophyllene (1) indicate the existence of two conformational isomers, beta alpha and beta beta, in each compound. At 25 degrees C, the beta alpha conformer predominates in 3 and 7 but the beta beta conformer predominates in 6. The higher percentage of 6 beta beta possibly derives from an intramolecular hydrogen bond. The treatment of 3, 6 and 7 with m-CPBA generates, in each case, two diastereomeric 4,5-epoxi-derivatives. The epoxides obtained from 6 have been isolated and analysed separately.

引用

页码：3813 / 3822

页数：10

共 16 条

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