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

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2013年 / 78卷 / 06期

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

页码：2802 / 2807

页数：6

共 49 条

[41] Transition-metal catalyzed oxidative cross-coupling reactions to form C-C bonds involving organometallic reagents as nucleophiles [J].

Shi, Wei ;

Liu, Chao ;

Lei, Aiwen .

CHEMICAL SOCIETY REVIEWS, 2011, 40 (05) :2761-2776

[42] Concise and efficient synthesis of calothrixin B [J].

Sissouma, Drissa ;

Maingot, Lucie ;

Collet, Sylvain ;

Guingant, Andre .

JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (22) :8384-8389

[43] A biomimetic synthesis of calothrixin B [J].

Sperry, Jonathan ;

McErlean, Christopher S. P. ;

Slawin, Alexandra M. Z. ;

Moody, Christopher J. .

TETRAHEDRON LETTERS, 2007, 48 (02) :231-234

[44] Direct C-H Transformation via Iron Catalysis [J].

Sun, Chang-Liang ;

Li, Bi-Jie ;

Shi, Zhang-Jie .

CHEMICAL REVIEWS, 2011, 111 (03) :1293-1314

[45] A facile synthesis of antitumoral indeno[1,2-c]pyrazole-4-one by mild oxidation with molecular oxygen [J].

Tao, ZF ;

Sowin, TJ ;

Lin, NH .

TETRAHEDRON LETTERS, 2005, 46 (44) :7615-7618

[46] A new total synthesis of an indolo[3,2-j]phenanthridine alkaloid calothrixin B [J].

Tohyama, S ;

Choshi, T ;

Matsumoto, K ;

Yamabuki, A ;

Ikegata, K ;

Nobuhiro, J ;

Hibino, S .

TETRAHEDRON LETTERS, 2005, 46 (32) :5263-5264

[47] TOTAL SYNTHESIS OF BIOACTIVE INDOLO[3,2-j]PHENANTHRIDINE ALKALOID, CALOTHRIXIN B [J].

Tohyama, Shigeo ;

Choshi, Tominari ;

Matsumoto, Kohji ;

Yamabuki, Akira ;

Hieda, Yuhzo ;

Nobuhiro, Junko ;

Hibino, Satoshi .

HETEROCYCLES, 2010, 82 (01) :397-416

[48] Ag-mediated reactions: Coupling and heterocyclization reactions [J].

Weibel, Jean-Marc ;

Blanc, Aurelien ;

Pale, Patrick .

CHEMICAL REVIEWS, 2008, 108 (08) :3149-3173

[49] A biomimetic synthesis of the indolo[3,2-j]phenanthridine alkaloid, calothrixin B [J].

Yamabuki, Akira ;

Fujinawa, Hikohito ;

Choshi, Tominari ;

Tohyama, Shigeo ;

Matsumoto, Kohji ;

Ohmura, Kana ;

Nobuhiro, Junko ;

Hibino, Satoshi .

TETRAHEDRON LETTERS, 2006, 47 (33) :5859-5861

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