Total Synthesis of Calothrixin B and Its Analogs

被引:23
作者
Saravanan, Velu [1 ]
Ramalingam, Bose Muthu [1 ]
Mohanakrishnan, Arasambattu K. [1 ]
机构
[1] Univ Madras, Dept Organ Chem, Madras 600025, Tamil Nadu, India
关键词
Total synthesis; Natural products; Alkaloids; Nitrogen heterocycles; Electrocyclic reactions; Cyclization; DOMINO REACTION; CYANOBACTERIA; ROUTE;
D O I
10.1002/ejoc.201301524
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The total synthesis of calothrixin B and its analogs was achieved starting from 2-methylindole. The synthesis involved an electrocyclization of 2-nitroarylvinyl-3-phenylsulfonylvinylindoles as a key step to give 2-nitroaryl-4-methoxy-3-methylcarbazoles. Oxidation of these compounds followed by reductive cyclization led to N-phenylsulfonylquinocarbazoles. These quinocarbazoles underwent hydrolysis and aerial oxidation in one pot to give the target compounds.
引用
收藏
页码:1266 / 1279
页数:14
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