Formation of radicals by irradiation of alkyl halides in the presence of triethylamine.: Application to the synthesis of (±)-bisabolangelone

被引:20
作者
Cossy, J [1 ]
Bellosta, V [1 ]
Ranaivosata, JL [1 ]
Gille, B [1 ]
机构
[1] ESPCI, CNRS, Chim Organ Lab, F-75231 Paris 05, France
关键词
radicals; photoreductive cyclization; bisabolangelone;
D O I
10.1016/S0040-4020(01)00357-X
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The irradiation of unsaturated halides in the presence of triethylamine leads to the formation of the corresponding cyclized products. This photoreductive cyclization has been used to synthesize the bicyclic core of (+/-)-bisabolangelone. (C) 2001 Elsevier Science Ltd. AU rights reserved.
引用
收藏
页码:5173 / 5182
页数:10
相关论文
共 47 条
[31]  
Markó IE, 1999, ANGEW CHEM INT EDIT, V38, P3207, DOI 10.1002/(SICI)1521-3773(19991102)38:21<3207::AID-ANIE3207>3.0.CO
[32]  
2-I
[33]   SUBSTANCES PRESENT IN ANGELICA-SILVESTRIS AND HERACLEUM-SPHONDYLIUM HAVING AN ANTI-APPETITIVE EFFECT ON PHYTOPHAGIC INSECTS [J].
MUCKENSTURM, B ;
DUPLAY, D ;
ROBERT, PC ;
SIMONIS, MT ;
KIENLEN, JC .
BIOCHEMICAL SYSTEMATICS AND ECOLOGY, 1981, 9 (04) :289-292
[34]  
Narasaka K., 1987, ORG SYNTH, V65, P12
[35]  
NAVROT J, 1984, BIOCH SYST ECOL, V12, P99
[36]  
NOVOTNY L, 1966, TETRAHEDRON LETT, V30, P2541
[37]   SILYLATED DERIVATIVES OF ARABINONUCLEOSIDES [J].
OGILVIE, KK ;
HAKIMELAHI, GH ;
PROBA, ZA ;
MCGEE, DPC .
TETRAHEDRON LETTERS, 1982, 23 (19) :1997-2000
[38]  
POIGNY S, 1999, THESIS U PARIS 6 FRA
[39]   TOTAL, ASYMMETRIC-SYNTHESIS OF (+)-CASTANOSPERMINE, (+)-6-DEOXYCASTANOSPERMINE, AND (+)-6-DEOXY-6-FLUOROCASTANOSPERMINE [J].
REYMOND, JL ;
PINKERTON, AA ;
VOGEL, P .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (06) :2128-2135
[40]   TOTAL SYNTHESIS OF (+/-) BISABOLANGELONE [J].
RISS, B ;
MUCKENSTURM, B .
TETRAHEDRON, 1989, 45 (09) :2591-2604