Palladium-catalysed N-annulation routes to indoles: the synthesis of indoles with sterically demanding N-substituents, including demethylasterriquinone A1

被引:62
作者
Fletcher, Anthony J.
Bax, Matthew N.
Willis, Michael C.
机构
[1] Univ Oxford, Dept Chem, Chem Res Lab, Oxford OX1 3TA, England
[2] Univ Bath, Dept Chem, Bath BA2 7AY, Avon, England
关键词
D O I
10.1039/b712227f
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Tandem palladium-catalysed aryl and alkenyl C-N bond formation allows the synthesis of a variety of indoles bearing sterically demanding N-substituents, including the natural product demethylasterriquinone A1.
引用
收藏
页码:4764 / 4766
页数:3
相关论文
共 38 条
[1]   Serotonin 5-HT2 receptor, dopamine D-2 receptor, and alpha(1) adrenoceptor antagonists. Conformationally flexible analogues of the atypical antipsychotic sertindole [J].
Andersen, K ;
Liljefors, T ;
Hyttel, J ;
Perregaard, J .
JOURNAL OF MEDICINAL CHEMISTRY, 1996, 39 (19) :3723-3738
[2]  
[Anonymous], 2002, HDB ORGANOPALLADIUM
[3]   METABOLIC PRODUCTS OF ASPERGILLUS-TERREUS .10. BIOSYNTHESIS OF ASTERRIQUINONES [J].
ARAI, K ;
YAMAMOTO, Y .
CHEMICAL & PHARMACEUTICAL BULLETIN, 1990, 38 (11) :2929-2932
[4]   Short, enantioselective total synthesis of okaramine N [J].
Baran, PS ;
Guerrero, CA ;
Corey, EJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (19) :5628-5629
[5]   A stereoselective synthetic approach to (2S,3R)-N-(1′ 1′-dimethyl-2′,3′-epoxypropyl)-3-hydroxytryptophan, a component of cyclomarin A [J].
Hansen, DB ;
Lewis, AS ;
Gavalas, SJ ;
Joullié, MM .
TETRAHEDRON-ASYMMETRY, 2006, 17 (01) :15-21
[6]   NEUROLEPTIC ACTIVITY IN 5-ARYLTETRAHYDRO-GAMMA-CARBOLINES [J].
HARBERT, CA ;
PLATTNER, JJ ;
WELCH, WM ;
WEISSMAN, A ;
KOE, BK .
JOURNAL OF MEDICINAL CHEMISTRY, 1980, 23 (06) :635-643
[7]   A one-pot, two-step synthesis of tetrahydro asterriquinone E [J].
Harris, GD ;
Nguyen, A ;
App, H ;
Hirth, P ;
McMahon, G ;
Tang, C .
ORGANIC LETTERS, 1999, 1 (03) :431-433
[8]  
Hartwig J. F., 2002, HDB ORGANOPALLADIUM, V1, P1097, DOI DOI 10.1002/0471212466.CH43
[9]   Expanding Pd-catalyzed C-N bond-forming processes: The first amidation of aryl sulfonates, aqueous amination, and complementarity with Cu-catalyzed reactions [J].
Huang, XH ;
Anderson, KW ;
Zim, D ;
Jiang, L ;
Klapars, A ;
Buchwald, SL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (22) :6653-6655
[10]   3-indolyl-1-naphthylmethanes:: New cannabimimetic Indoles provide evidence for aromatic stacking interactions with the CB1 cannabinoid receptor [J].
Huffman, JW ;
Mabon, R ;
Wu, MJ ;
Lu, JZ ;
Hart, R ;
Hurst, DP ;
Reggio, PH ;
Wiley, JL ;
Martin, BR .
BIOORGANIC & MEDICINAL CHEMISTRY, 2003, 11 (04) :539-549