JUNICEDRANOL, A SESQUITERPENE WITH A NOVEL CARBON SKELETON FROM JUNIPERUS-OXYCEDRUS SSP MACROCARPA

被引:14
作者
BARRERO, AF
ALVAREZMANZANEDA, E
LARA, A
机构
[1] Departamento de Química Orgánica, Facultad de Ciencias, Universidad de Granada
关键词
D O I
10.1016/0040-4039(95)01228-A
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Junicedranol 1, a sesquiterpene with a novel carbon skeleton, has been isolated from the essential oil of the wood of Juniperus oxycedrus ssp. macrocarpa. The structure was determined by the analysis of 2D NMR spectra to be a 2,2,6,7-teaamethyl-tricycle[5.2.2.0(1.6)]undecane carbon skeleton. Its relative stereochemistry is proposed on the basis of NOESY. The absolute configuration was established by ''Mosher's method''.
引用
收藏
页码:6347 / 6350
页数:4
相关论文
共 7 条
[1]   EVIDENCES ABOUT THE STEREOCHEMISTRY OF 14-HYDROXY-9-EPI-BETA-CARYOPHYLLENE [J].
BARRERO, AF ;
OLTRA, JE ;
BARRAGAN, A .
TETRAHEDRON LETTERS, 1990, 31 (28) :4069-4072
[2]   OXYGENATED SESQUITERPENES FROM THE WOOD OF JUNIPERUS-OXYCEDRUS [J].
BARRERO, AF ;
SANCHEZ, JF ;
OLTRA, JE ;
ALTAREJOS, J ;
FERROL, N ;
BARRAGAN, A .
PHYTOCHEMISTRY, 1991, 30 (05) :1551-1554
[3]   STEREOCHEMISTRY OF 14-HYDROXY-BETA-CARYOPHYLLENE AND RELATED-COMPOUNDS [J].
BARRERO, AF ;
MOLINA, J ;
OLTRA, JE ;
ALTAREJOS, J ;
BARRAGAN, A ;
LARA, A ;
SEGURA, M .
TETRAHEDRON, 1995, 51 (13) :3813-3822
[4]  
Barrero Alejandro F., 1993, Flavour and Fragrance Journal, V8, P185, DOI 10.1002/ffj.2730080404
[5]   NUCLEAR MAGNETIC-RESONANCE ENANTIOMER REAGENTS - CONFIGURATIONAL CORRELATIONS VIA NUCLEAR MAGNETIC-RESONANCE CHEMICAL-SHIFTS OF DIASTEREOMERIC MANDELATE, O-METHYLMANDELATE, AND ALPHA-METHOXY-ALPHA-TRIFLUOROMETHYLPHENYLACETATE (MTPA) ESTERS [J].
DALE, JA ;
MOSHER, HS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (02) :512-519
[6]   PYRIDINE-INDUCED SOLVENT SHIFTS IN NUCLEAR MAGNETIC RESONANCE SPECTRA OF HYDROXYLIC COMPOUNDS [J].
DEMARCO, PV ;
FARKAS, E ;
DODDRELL, D ;
MYLARI, BL ;
WENKERT, E .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1968, 90 (20) :5480-&
[7]   HIGH-FIELD FT NMR APPLICATION OF MOSHER METHOD - THE ABSOLUTE-CONFIGURATIONS OF MARINE TERPENOIDS [J].
OHTANI, I ;
KUSUMI, T ;
KASHMAN, Y ;
KAKISAWA, H .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (11) :4092-4096