Regioselective intramolecular reactions of 2-indolylacyl radicals with pyridines: A direct synthetic entry to ellipticine quinones

被引:33
作者
Bennasar, ML [1 ]
Roca, T [1 ]
Ferrando, F [1 ]
机构
[1] Univ Barcelona, Fac Pharm, Organ Chem Lab, E-08028 Barcelona, Spain
关键词
D O I
10.1021/jo0514974
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHIC] 2-Indolylacyl radicals generated from the corresponding selenoesters under hexabutylditin-hv conditions undergo regioselective intramolecular reaction with unprotonated pyridines to give polycyclic indolylpyridyl ketones. For substrates bearing a (3-pyridyl)methyl moiety connected to the 3-position of the indole ring, the cyclization provides easy access to ellipticine quinones.
引用
收藏
页码:9077 / 9080
页数:4
相关论文
共 53 条
[1]   Bu3SnH mediated oxidative radical cyclisation onto imidazoles and pyrroles [J].
Aldabbagh, F ;
Bowman, WR ;
Mann, E ;
Slawin, AMZ .
TETRAHEDRON, 1999, 55 (26) :8111-8128
[2]   Synthetic applications of aryl radical building blocks for cyclisation onto azoles [J].
Allin, SM ;
Bowman, WR ;
Elsegood, MRJ ;
McKee, V ;
Karim, R ;
Rahman, SS .
TETRAHEDRON, 2005, 61 (10) :2689-2696
[3]   Radical cyclisation onto pyrazoles: synthesis of withasomnine [J].
Allin, SM ;
Barton, WRS ;
Bowman, WR ;
McInally, T .
TETRAHEDRON LETTERS, 2002, 43 (23) :4191-4193
[4]   Acyl radical cyclisation onto pyrroles [J].
Allin, SM ;
Barton, WRS ;
Bowman, WR ;
McInally, T .
TETRAHEDRON LETTERS, 2001, 42 (44) :7887-7890
[5]   OXIDATIVE RADICAL CYCLIZATION OF (OMEGA-IODOALKYL)INDOLES AND PYRROLES - SYNTHESIS OF (-)-MONOMORINE AND 3 DIASTEREOMERS [J].
ARTIS, DR ;
CHO, IS ;
JAIMEFIGUEROA, S ;
MUCHOWSKI, JM .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (09) :2456-2466
[6]   Tin-free radical cyclizations for the synthesis of 7-azaoxindoles, 7-azaindolines, tetrahydro[1,8]naphthyridines, and tetrahydro-5H-pyrido[2,3-b]azepin-8-ones [J].
Bacqué, E ;
El Qacemi, M ;
Zard, SZ .
ORGANIC LETTERS, 2004, 6 (21) :3671-3674
[7]   The mechanism of Bu3SnH-mediated homolytic aromatic substitution [J].
Beckwith, ALJ ;
Bowry, VW ;
Bowman, WR ;
Mann, E ;
Parr, J ;
Storey, JMD .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (01) :95-98
[8]   Intramolecular reactions of 2-indolylacyl radicals: cyclisation upon aromatic rings [J].
Bennasar, ML ;
Roca, T ;
Ferrando, F .
TETRAHEDRON LETTERS, 2004, 45 (29) :5605-5609
[9]   Intramolecular reactions of 2-indolylacyl radicals: Access to 1,2-fused ring indole derivatives [J].
Bennasar, ML ;
Roca, T ;
Ferrando, F .
ORGANIC LETTERS, 2004, 6 (05) :759-762
[10]   Generation and intermolecular reactions of 3-indolylacyl radicals [J].
Bennasar, ML ;
Roca, T ;
Griera, R ;
Bassa, M ;
Bosch, J .
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (17) :6268-6271