REGIOCHEMICAL AND STEREOCHEMICAL VARIATIONS IN DIELS-ALDER REACTIONS

被引:17
作者
ARSENIYADIS, S [1 ]
RODRIGUEZ, R [1 ]
YASHUNSKY, DV [1 ]
CAMARA, J [1 ]
OURISSON, G [1 ]
机构
[1] UNIV STRASBOURG 1,CNRS,CHIM ORGAN SUBSTANCES NAT LAB,F-67084 STRASBOURG,FRANCE
关键词
D O I
10.1016/S0040-4039(00)76983-8
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The AB+D --> ABCD approach for the synthesis of the tetracyclic intermediates 3-6 is reinvestigated. Water, high-pressure, LiCl and scandium triflate-mediated Diels-Alder reactions of 1 and 2 are reported.
引用
收藏
页码:4843 / 4846
页数:4
相关论文
共 11 条
[1]   TRITERPENE ALCOHOL ISOLATION FROM OIL SHALE [J].
ALBRECHT, P ;
OURISSON, G .
SCIENCE, 1969, 163 (3872) :1192-&
[2]  
ALDER K, 1951, LIEBIGS ANN CHEM, V571, P87
[3]   DIELS-ALDER APPROACHES TO PENTACYCLIC TRITERPENES OF THE ARBORANE AND THE FERNANE FAMILIES [J].
ARSENIYADIS, S ;
RODRIGUEZ, R ;
CAMARA, J ;
GUITTET, E ;
TOUPET, L .
TETRAHEDRON LETTERS, 1993, 34 (07) :1141-1144
[4]   SYNTHETIC APPROACHES TO PENTACYCLIC TRITERPENES OF THE ARBORANE FAMILY .2. TETRACYCLIC INTERMEDIATES [J].
ARSENIYADIS, S ;
RODRIGUEZ, R ;
SPANEVELLO, R ;
CAMARA, J ;
THOMPSON, A ;
GUITTET, E ;
OURISSON, G .
TETRAHEDRON, 1992, 48 (07) :1255-1262
[5]   HYDROPHOBIC EFFECTS ON SIMPLE ORGANIC-REACTIONS IN WATER [J].
BRESLOW, R .
ACCOUNTS OF CHEMICAL RESEARCH, 1991, 24 (06) :159-164
[6]  
BRESLOW R, 1980, J AM CHEM SOC, V102, P7816
[7]  
DASTILLUNG M, 1980, J CHEM RES S, V168, P2353
[8]   SCANDIUM TRIFLUOROMETHANESULFONATE (SC(OTF)3) - A NOVEL REUSABLE CATALYST IN THE DIELS-ALDER REACTION [J].
KOBAYASHI, S ;
HACHIYA, I ;
ARAKI, M ;
ISHITANI, H .
TETRAHEDRON LETTERS, 1993, 34 (23) :3755-3758
[9]   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
[10]   HOPANOIDS .2. BIOHOPANOIDS - A NOVEL CLASS OF BACTERIAL LIPIDS [J].
OURISSON, G ;
ROHMER, M .
ACCOUNTS OF CHEMICAL RESEARCH, 1992, 25 (09) :403-408