Pd-Catalyzed Chemoselective Catellani Ortho-Arylation of Iodopyrroles: Rapid Total Synthesis of Rhazinal

被引:99
作者
Sui, Xianwei [1 ]
Zhu, Rui [1 ]
Li, Gencheng [1 ]
Ma, Xinna [1 ]
Gu, Zhenhua [1 ]
机构
[1] Univ Sci & Technol China, Dept Chem, Hefei 230026, Anhui, Peoples R China
基金
中国国家自然科学基金;
关键词
TETRASUBSTITUTED HELICAL ALKENES; H BOND ACTIVATION; CONCISE SYNTHESIS; ARYL IODIDES; PALLADIUM; ALKYLATION; HETEROCYCLES; INDOLES; ANNULATION; SEQUENCE;
D O I
10.1021/ja404494u
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A Pd-catalyzed chemoselective Catellani reaction of iodopyrroles was developed. The rare chemoselectivity between two,different aryl halides was realized by optimizing the kinetics of the different steps of this multicomponent process. The new developed method led to the rapid synthesis of rhazinal in a highly efficient manner.
引用
收藏
页码:9318 / 9321
页数:4
相关论文
共 61 条
[1]   OCCURRENCE OF GEISSOSCHIZINE AND OTHER MINOR BIOGENETICALLY RELATED ALKALOIDS IN RHAZYA-STRICTA [J].
BANERJI, A ;
MAJUMDER, PL ;
CHATTERJEE, A .
PHYTOCHEMISTRY, 1970, 9 (07) :1491-+
[2]  
Banwell MG, 2006, ARKIVOC, P163
[3]   Total synthesis of (±)-rhazinal, an alkaloidal spindle toxin from Kopsia teoi [J].
Banwell, MG ;
Edwards, AJ ;
Jolliffe, KA ;
Smith, JA ;
Hamel, E ;
Verdier-Pinard, P .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2003, 1 (02) :296-305
[4]   Synthesis and biological evaluation of A-ring biaryl-carbamate analogues of rhazinilam [J].
Baudoin, O ;
Claveau, F ;
Thoret, S ;
Herrbach, A ;
Guénard, D ;
Guéritte, F .
BIOORGANIC & MEDICINAL CHEMISTRY, 2002, 10 (11) :3395-3400
[5]   Synthesis of rhazinicine by a metal-catalyzed C-H bond functionalization strategy [J].
Beck, Elizabeth M. ;
Hatley, Richard ;
Gaunt, Matthew J. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (16) :3004-3007
[6]   Concise synthesis of (±)-rhazinilam through direct coupling [J].
Bowie, AL ;
Hughes, CC ;
Trauner, D .
ORGANIC LETTERS, 2005, 7 (23) :5207-5209
[7]   Total Synthesis of (±)-Rhazinal Using Novel Palladium-Catalyzed Cyclizations [J].
Bowie, Alfred L., Jr. ;
Trauner, Dirk .
JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (04) :1581-1586
[8]   Exploiting the Chemistry of Strained Rings: Synthesis of Indoles via Domino Reaction of Aryl Iodides with 2H-Azirines [J].
Candito, David A. ;
Lautens, Mark .
ORGANIC LETTERS, 2010, 12 (15) :3312-3315
[9]   Aryl transfer between Pd(II) centers or Pd(IV) intermediates in Pd-catalyzed domino reactions [J].
Cárdenas, DJ ;
Martín-Matute, B ;
Echavarren, AM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (15) :5033-5040
[10]   Catalytic multistep reactions via palladacycles [J].
Catellani, M .
SYNLETT, 2003, (03) :298-313