Total Synthesis of (+)-Isatisine A

被引:128
作者
Karadeolian, Avedis [1 ]
Kerr, Michael A. [1 ]
机构
[1] Univ Western Ontario, Dept Chem, London, ON N6A 5B7, Canada
基金
加拿大自然科学与工程研究理事会;
关键词
alkaloids; asymmetric synthesis; heterocycles; isatisine A; total synthesis; DONOR-ACCEPTOR CYCLOPROPANES; 3+2 CYCLOADDITION; ALDEHYDES; OXIDATION; INDOLES; ACID; TETRAHYDROFURANS;
D O I
10.1002/anie.200906632
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
(Figure Presented) Isatis indigotica has long been used as a source of therapeutic compounds in traditional Chinese medicine (the roots are the source of Ben Lan Gen herbal tea). In 2007 the leaves of J. indigotica yielded isatisine A, an unusual oxidized bisindole. A concise, enantiospecific total synthesis of isatisine A is reported using a homochiral cyclopropane diester to construct the key tetrahydrofuran ring. © 2010 Wiley-VCH Verlag GmbH & Co. KGaA,.
引用
收藏
页码:1133 / 1135
页数:3
相关论文
共 21 条
[1]   Radical intermediates in the peroxidation of indoles [J].
Astolfi, P ;
Greci, L ;
Rizzoli, C ;
Sgarabotto, P ;
Marrosu, G .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 2001, (09) :1634-1640
[2]  
Buller MJ, 2007, HETEROCYCLES, V72, P163
[3]   Asymmetric Synthesis of (+)-Polyanthellin A [J].
Campbell, Matthew J. ;
Johnson, Jeffrey S. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (30) :10370-+
[4]  
Carson C. A., 2006, ANGEW CHEM, V118, P6710
[5]   Total synthesis of (+)-phyllantidine [J].
Carson, Cheryl A. ;
Kerr, Michael A. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (39) :6560-6563
[6]  
CHIEN CS, 1984, CHEM PHARM BULL, V32, P3945
[7]  
COLANDREA VJ, 1996, ORG LETT, V37, P6049
[8]   Two syntheses of the 16- and 17-membered DEF ring systems of chloropeptin and complestatin [J].
Elder, AM ;
Rich, DH .
ORGANIC LETTERS, 1999, 1 (09) :1443-1446
[9]   Oxidation of indole substrates by oxodiperoxomolybdenum-trialkyl(aryl) - phosphine oxide complexes [J].
Kiraz, CIA ;
Emge, TJ ;
Jimenez, LS .
JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (06) :2200-2202
[10]   Isatisine a, a novel alkaloid with an unprecedented skeleton from leaves of isatis indigotica [J].
Liu, Ji-Feng ;
Jiang, Zhi-Yong ;
Wang, Rui-Rui ;
Zheng, Yong-Tang ;
Chen, Ji-Jun ;
Zhang, Xue-Mei ;
Ma, Yun-Bao .
ORGANIC LETTERS, 2007, 9 (21) :4127-4129