Palladium-mediated intramolecular biaryl coupling reaction for natural product synthesis

被引:30
作者
Abe, Hitoshi [1 ]
Harayama, Takashi [2 ]
机构
[1] Okayama Univ, Adv Sci Res Ctr, Okayama 7008530, Japan
[2] Tokushima Bunri Univ, Fac Pharmaceut Sci, Sanuki, Kagawa 7692193, Japan
关键词
palladium; phenanthridine; lactone; C-H activation; biphenyl;
D O I
10.3987/REV-07-627
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An intramoleculer biaryl coupling reaction is a useful technique for the synthesis of certain types of heterocyclic compounds. This short review describes recent advances in the Pd-mediated intramolecular C-C bond formation reaction between two aromatic rings, and several examples of natural product synthesis using this reaction. The mechanistic aspect of this reaction is also explained.
引用
收藏
页码:1305 / 1320
页数:16
相关论文
共 114 条
[1]   Synthesis of graphislactones A-D through a palladium-mediated biaryl coupling reaction of phenyl benzoate derivatives [J].
Abe, H ;
Nishioka, K ;
Takeda, S ;
Arai, M ;
Takeuchi, Y ;
Harayama, T .
TETRAHEDRON LETTERS, 2005, 46 (18) :3197-3200
[2]   Enantioselective construction of biaryl part in the synthesis of stegane related compounds [J].
Abe, H ;
Takeda, S ;
Fujita, T ;
Nishioka, K ;
Takeuchi, Y ;
Harayama, T .
TETRAHEDRON LETTERS, 2004, 45 (11) :2327-2329
[3]   Enantioselective synthesis of valoneic acid derivative [J].
Abe, Hitoshi ;
Sahara, Yusuke ;
Matsuzaki, Yuki ;
Takeuchi, Yasuo ;
Harayama, Takashi .
TETRAHEDRON LETTERS, 2008, 49 (04) :605-609
[4]   Synthesis of alternariol through an intramolecular biaryl coupling reaction using palladium reagent [J].
Abe, Hitoshi ;
Fukumoto, Tomoko ;
Takeuchi, Yasuo ;
Harayama, Takashi .
HETEROCYCLES, 2007, 74 :265-271
[5]  
Abe H, 2006, HETEROCYCLES, V69, P217
[6]   PALLADIUM-CATALYZED CYCLIZATION OF 2-SUBSTITUTED HALOGENOARENES BY DEHYDROHALOGENATION [J].
AMES, DE ;
OPALKO, A .
TETRAHEDRON, 1984, 40 (10) :1919-1925
[7]  
ASAHINA Y, 1915, YAKUGAKU ZASSHI, V35, P1273
[8]   TOTAL SYNTHESIS OF ANTI-LEUKEMIC LIGNAN (+/-)-STEGANACIN [J].
BECKER, D ;
HUGHES, LR ;
RAPHAEL, RA .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1977, (14) :1674-1681
[9]   STUDIES OF RUTAECARPINE AND RELATED QUINAZOLINOCARBOLINE ALKALOIDS [J].
BERGMAN, J ;
BERGMAN, S .
JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (08) :1246-1255
[10]  
BERGMAN J, 1985, ALKALOIDS, V26, P30