Diversity-Oriented Synthesis of Calothrixins and Ellipticines

被引:22
作者
Dethe, Dattatraya H. [1 ]
Murhade, Ganesh M. [1 ]
机构
[1] Indian Inst Technol, Dept Chem, Kanpur 208016, Uttar Pradesh, India
关键词
Natural products; Nitrogen heterocycles; Quinones; Rearrangement; Oxidation; FACILE SYNTHESIS; LEAD-TETRAACETATE; ROUTE; DERIVATIVES; ALKALOIDS; ANALOGS; ENTRY;
D O I
10.1002/ejoc.201402837
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The divergent synthesis of calothrixins and ellipticines has been accomplished by utilising the one-pot formation of o-diacylarenes as a key intermediate through rearrangement of o-hydroxy ketone monoacyl hydrazones by lead tetraacetate mediated oxidation.
引用
收藏
页码:6953 / 6962
页数:10
相关论文
共 60 条
[1]   Total Synthesis of Calothrixins A and B by Palladium-Catalyzed Tandem Cyclization/Cross-Coupling Reaction of Indolylborate [J].
Abe, Takumi ;
Ikeda, Toshiaki ;
Choshi, Tominari ;
Hibino, Satoshi ;
Hatae, Noriyuki ;
Toyata, Eiko ;
Yanada, Reiko ;
Ishikura, Minoru .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2012, 2012 (26) :5018-5027
[2]   Concise Total Synthesis of Calothrixins A and B [J].
Abe, Takumi ;
Ikeda, Toshiaki ;
Yanada, Reiko ;
Ishikura, Minoru .
ORGANIC LETTERS, 2011, 13 (13) :3356-3359
[3]  
Alvarez M, 2001, ALKALOIDS, V57, P235, DOI 10.1016/S0099-9598(01)57005-4
[4]  
Alvarez M., 1994, CHEM HETEROCYCLIC CO, P261
[5]  
[Anonymous], 1990, ADV HETEROCYCLIC NAT
[6]   A new radical-based route to calothrixin B [J].
Bennasar, ML ;
Roca, T ;
Ferrando, F .
ORGANIC LETTERS, 2006, 8 (04) :561-564
[7]   Regioselective intramolecular reactions of 2-indolylacyl radicals with pyridines: A direct synthetic entry to ellipticine quinones [J].
Bennasar, ML ;
Roca, T ;
Ferrando, F .
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (22) :9077-9080
[8]   Structure-activity delineation of quinones related to the biologically active Calothrixin B [J].
Bernardo, Paul H. ;
Chai, Christina L. L. ;
Le Guen, Maurice ;
Smith, Geoffrey D. ;
Waring, Paul .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2007, 17 (01) :82-85
[9]   Synthesis, electrochemistry, and bioactivity of the cyanobacterial calothrixins and related quinones [J].
Bernardo, PH ;
Chai, CLL ;
Heath, GA ;
Mahon, PJ ;
Smith, GD ;
Waring, P ;
Wilkes, BA .
JOURNAL OF MEDICINAL CHEMISTRY, 2004, 47 (20) :4958-4963
[10]   Friedel-Crafts acylation and metalation strategies in the synthesis of calothrixins A and B [J].
Bernardo, PH ;
Chai, CLL .
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (23) :8906-8909