A general synthesis of phenanthridinone alkaloids

被引:17
作者
Afarinkia, Kamyar [1 ]
Ndibwami, Alex [1 ]
机构
[1] Univ Bradford, Inst Canc Therapeut, Bradford BD1 7DP, W Yorkshire, England
关键词
Diets-Alder cycloadditions; stereoselectivity; regioselectivity;
D O I
10.1055/s-2007-984540
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
We report a general synthesis of the phenanthridinone skeleton using functionally rich, bridged bicyclic lactones obtained from the Diels-Alder cycloadditions of 3-bromo-2(H)-pyran-2-one.
引用
收藏
页码:1940 / 1944
页数:5
相关论文
共 41 条
[1]   An experimental and computational investigation of the Diels-Alder cycloadditions of halogen-substituted 2(H)-pyran-2-ones [J].
Afarinkia, K ;
Bearpark, MJ ;
Ndibwami, A .
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (04) :1122-1133
[2]   Computational and experimental investigation of the Diels-Alder cycloadditions of 4-chloro-2(H)-pyran-2-one [J].
Afarinkia, K ;
Bearpark, MJ ;
Ndibwami, A .
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (19) :7158-7166
[3]   5-BROMO-2-PYRONE - AN EASILY PREPARED AMBIPHILIC DIENE AND A SYNTHETIC EQUIVALENT OF 2-PYRONE IN MILD, THERMAL, DIELS-ALDER CYCLOADDITIONS [J].
AFARINKIA, K ;
POSNER, GH .
TETRAHEDRON LETTERS, 1992, 33 (51) :7839-7842
[4]   Unusual stereoselectivity in Diels-Alder cycloadditions of 5-bromopyrone [J].
Afarinkia, K ;
Daly, NT ;
GomezFarnos, S ;
Joshi, S .
TETRAHEDRON LETTERS, 1997, 38 (13) :2369-2372
[5]   DIELS-ALDER CYCLOADDITIONS OF 2-PYRONES AND 2-PYRIDONES [J].
AFARINKIA, K ;
VINADER, V ;
NELSON, TD ;
POSNER, GH .
TETRAHEDRON, 1992, 48 (42) :9111-9171
[6]   A novel and concise synthesis of (±)2-epi-validamine [J].
Afarinkia, K ;
Mahmood, F .
TETRAHEDRON, 1999, 55 (10) :3129-3140
[7]   A CONVENIENT SYNTHESIS OF ISOTOPICALLY LABELED ANTHRAQUINONES, CHRYSOPHANOL, ISLANDICIN, AND EMODIN - INCORPORATION OF [METHYL-2H3]CHRYSOPHANOL INTO TAJIXANTHONE IN ASPERGILLUS-VARIECOLOR [J].
AHMED, SA ;
BARDSHIRI, E ;
SIMPSON, TJ .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1987, (12) :883-884
[8]   TOTAL SYNTHESES OF AZAFLUORANTHENE ALKALOIDS - RUFESCINE AND IMELUTEINE [J].
BOGER, DL ;
BROTHERTON, CE .
JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (21) :4050-4055
[10]  
CARASCO L, 1975, FEBS LETT, V52, P236