SYNTHETIC APPROACHES TO PENTACYCLIC TRITERPENES OF THE ARBORANE FAMILY .2. TETRACYCLIC INTERMEDIATES

被引:10
作者
ARSENIYADIS, S [1 ]
RODRIGUEZ, R [1 ]
SPANEVELLO, R [1 ]
CAMARA, J [1 ]
THOMPSON, A [1 ]
GUITTET, E [1 ]
OURISSON, G [1 ]
机构
[1] CTR NEUROCHIM, F-67084 STRASBOURG, FRANCE
关键词
ISOARBORINOL; DIELS-ALDER REACTION; LEWIS ACID CATALYSIS; 2,6-DIMETHYLBENZOQUINONE;
D O I
10.1016/S0040-4020(01)90787-2
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Diels-Alder condensation of the bicyclic diene 1 with 2,6-dimethylbenzoquinone 2 under thermal and Lewis acid-catalyzed conditions gives the diastereomers 3, 4, 5 and 8; their structures are demonstrated by NMR analysis, in full agreement with the conformations deduced from molecular mechanics.
引用
收藏
页码:1255 / 1262
页数:8
相关论文
共 11 条
[1]   SYNTHETIC APPROACHES TO PENTACYCLIC TRITERPENES OF THE ARBORANE FAMILY [J].
ARSENIYADIS, S ;
RODRIGUEZ, R ;
CABRERA, E ;
THOMPSON, A ;
OURISSON, G .
TETRAHEDRON, 1991, 47 (34) :7045-7058
[2]   STEREOCHEMICAL VARIATIONS IN THE CYCLOCONDENSATION OF ALDEHYDES WITH SILOXYDIENES - AN APPLICATION TO THE ERYTHRONOLIDE SERIES [J].
DANISHEFSKY, S ;
LARSON, ER ;
ASKIN, D .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (23) :6457-6458
[3]   TOTAL SYNTHESIS OF STEROIDS .1. RING-A AROMATIC-COMPOUNDS - REGIOCONTROL IN DIENE ADDITIONS WITH 6-METHOXY-1-VINYL-3,4-DIHYDRONAPHTHALENE [J].
DAS, J ;
KUBELA, R ;
MACALPINE, GA ;
STOJANAC, Z ;
VALENTA, Z .
CANADIAN JOURNAL OF CHEMISTRY, 1979, 57 (24) :3308-3319
[4]   EXPERIMENTAL CHEMICAL-SHIFT CORRELATION MAPS IN NUCLEAR MAGNETIC-RESONANCE SPECTROSCOPY [J].
FREEMAN, R ;
MORRIS, GA .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1978, (16) :684-686
[5]   RESOLUTION AND ASSIGNMENT OF THE 270-MHZ PROTON SPECTRUM OF CELLOBIOSE BY HOMO-NUCLEAR AND HETERONUCLEAR TWO-DIMENSIONAL NMR [J].
HALL, LD ;
MORRIS, GA ;
SUKUMAR, S .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (05) :1745-1747
[6]  
KRAJEWSKIBERTRA.MA, 1991, THESIS U L PASTEUR S
[7]   TRICYCLOHEXAPRENOL AND AN OCTAPRENEDIOL, 2 OF THE PRIMITIVE AMPHIPHILIC LIPIDS DO IMPROVE PHOSPHOLIPIDIC MEMBRANES [J].
KRAJEWSKIBERTRAND, MA ;
HAYER, M ;
WOLFF, G ;
MILON, A ;
ALBRECHT, AM ;
HEISSLER, D ;
NAKATANI, Y ;
OURISSON, G .
TETRAHEDRON, 1990, 46 (09) :3143-3154
[8]   MECHANISTIC VARIATIONS IN THE LEWIS ACID-CATALYZED CYCLOCONDENSATION OF SILOXYDIENES WITH ALDEHYDES [J].
LARSON, ER ;
DANISHEFSKY, S .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (23) :6458-6460
[9]   PRECISE C-13 NMR MULTIPLICITY DETERMINATION [J].
LECOCQ, C ;
LALLEMAND, JY .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1981, (04) :150-152
[10]   PREDICTIVE MICROBIAL BIOCHEMISTRY - FROM MOLECULAR FOSSILS TO PROCARYOTIC MEMBRANES [J].
OURISSON, G ;
ALBRECHT, P ;
ROHMER, M .
TRENDS IN BIOCHEMICAL SCIENCES, 1982, 7 (07) :236-239