Total Synthesis of Calothrixin A and B via C-H Activation

被引:50
作者
Ramkumar, Nagarajan [1 ]
Nagarajan, Rajagopal [1 ]
机构
[1] Univ Hyderabad, Sch Chem, Hyderabad 500046, Andhra Pradesh, India
关键词
BIOMIMETIC SYNTHESIS; ALKALOIDS; CONCISE; ARYL; REDUCTION; CLEAVAGE; HALIDES; ETHERS; ESTERS; ROUTE;
D O I
10.1021/jo302821v
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Bioactive indolo[3,2-j]phenanthridine alkaloids Calothrixin A and B have been synthesized by exploiting Pd-catalyzed cross-coupling reaction via C-H activation as a key step starting from 4-methoxycarbazole.
引用
收藏
页码:2802 / 2807
页数:6
相关论文
共 49 条
[11]   PROGRESS TOWARDS THE TOTAL SYNTHESIS OF THE BIOACTIVE CALOTHRIXINS A AND B [J].
Choshi, Tominari ;
Hibino, Satoshi .
HETEROCYCLES, 2009, 77 (01) :85-97
[12]   Zinc-Catalyzed Reduction of Amides: Unprecedented Selectivity and Functional Group Tolerance [J].
Das, Shoubhik ;
Addis, Daniele ;
Zhou, Shaolin ;
Junge, Kathrin ;
Beller, Matthias .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (06) :1770-+
[13]  
de Meijere A., 2004, MetalCatalyzed CrossCoupling Reactions, V1
[14]   Coinage metal catalyzed C-H bond functionalization of hydrocarbons [J].
Diaz-Requejo, M. Mar ;
Perez, Pedro J. .
CHEMICAL REVIEWS, 2008, 108 (08) :3379-3394
[15]   Palladium-Catalysed Cross-Coupling of Vinyldisiloxanes with Benzylic and Allylic Halides and Sulfonates [J].
Frye, Elizabeth C. ;
O'Connor, Cornelius J. ;
Twigg, David G. ;
Elbert, Bryony ;
Laraia, Luca ;
Hulcoop, David G. ;
Venkitaraman, Ashok R. ;
Spring, David R. .
CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (28) :8774-8779
[16]   Practical Access to Amines by Platinum-Catalyzed Reduction of Carboxamides with Hydrosilanes: Synergy of Dual Si-H Groups Leads to High Efficiency and Selectivity [J].
Hanada, Shiori ;
Tsutsumi, Emi ;
Motoyama, Yukihiro ;
Nagashima, Hideo .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (41) :15032-15040
[17]   Synthesis of trisphaeridine and norchelerythrine through palladium-catalyzed aryl-aryl coupling reaction [J].
Harayama, T ;
Akamatsu, H ;
Okamura, K ;
Miyagoe, T ;
Akiyama, T ;
Abe, H ;
Takeuchi, Y .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2001, (05) :523-528
[18]   Aryl-aryl bond formation one century after the discovery of the Ullmann reaction [J].
Hassan, J ;
Sévignon, M ;
Gozzi, C ;
Schulz, E ;
Lemaire, M .
CHEMICAL REVIEWS, 2002, 102 (05) :1359-1469
[19]  
HO TL, 1977, SYNTHESIS-STUTTGART, P417
[20]   SYNTHETIC METHODS AND REACTIONS .29. CLEAVAGE OF ESTERS AND ETHERS WITH IODOTRIMETHYLSILANE [J].
HO, TL ;
OLAH, GA .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1976, 15 (12) :774-775