Novel regioselective synthesis of decahydrobenzocarbazoles using rhodium generated carbonyl ylides with indoles

被引：39

作者：

Muthusamy, S ^{[1
]}

Gunanathan, C ^{[1
]}

Babu, SA ^{[1
]}

机构：

[1] Cent Salt & Marine Chem Res Inst, Silicates & Catalysis Discipline, Bhavnagar 364002, Gujarat, India

来源：

TETRAHEDRON LETTERS | 2001年 / 42卷 / 03期

关键词：

diazo compounds; indoles; carbonyl ylides; cycloaddition; rhodium acetate catalyst;

D O I：

10.1016/S0040-4039(00)01990-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Intermolecular cycloadditions of five-membered cyclic carbonyl ylides 3 with indole, N-methylindole and N-benzylindole afforded decahydrobenzo[c]carbazole 4a-f or decahydrocyclopenta[c]carbazole 4g-h derivatives with high regioselectivity. With N-benzoylindole and N-sulphonylindole, decahydrobenzo[c]carbazoles 4i,j and the regioisomer decahydrobenzo[a]carbazoles 5i,j are isolated. The electron withdrawing substituent reduces both regioselectivity and reactivity of the cycloadditions. This methodology generated era-bridged (unnatural) decahydrobenzocarbazole derivatives with complete control of four stereocenters. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：523 / 526

页数：4