Synlett 2014; 25(16): 2289-2292
DOI: 10.1055/s-0034-1378372
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© Georg Thieme Verlag Stuttgart · New York

Shortcut Approach to Cyclopenta[b]indoles by [3+2] Cyclodimerization of Indole-Derived Cyclopropanes

Olga A. Ivanova
a  Department of Chemistry, M.V. Lomonosov Moscow State University, Leninskie gory 1-3, Moscow 119991, Russian Federation    Fax: +7(495)9391814   Email: ekatbud@kinet.chem.msu.ru
,
Ekaterina M. Budynina*
a  Department of Chemistry, M.V. Lomonosov Moscow State University, Leninskie gory 1-3, Moscow 119991, Russian Federation    Fax: +7(495)9391814   Email: ekatbud@kinet.chem.msu.ru
b  Laboratory of Chemical Synthesis, Federal Research Center of Pediatric Hematology, Oncology, and Immunology, Samory Mashela. 1, Moscow 117997, Russian Federation
,
Dmitriy A. Skvortsov
a  Department of Chemistry, M.V. Lomonosov Moscow State University, Leninskie gory 1-3, Moscow 119991, Russian Federation    Fax: +7(495)9391814   Email: ekatbud@kinet.chem.msu.ru
,
Igor V. Trushkov
a  Department of Chemistry, M.V. Lomonosov Moscow State University, Leninskie gory 1-3, Moscow 119991, Russian Federation    Fax: +7(495)9391814   Email: ekatbud@kinet.chem.msu.ru
b  Laboratory of Chemical Synthesis, Federal Research Center of Pediatric Hematology, Oncology, and Immunology, Samory Mashela. 1, Moscow 117997, Russian Federation
,
Mikhail Ya. Melnikov
a  Department of Chemistry, M.V. Lomonosov Moscow State University, Leninskie gory 1-3, Moscow 119991, Russian Federation    Fax: +7(495)9391814   Email: ekatbud@kinet.chem.msu.ru
› Author Affiliations
Further Information

Publication History

Received: 16 May 2014

Accepted after revision: 11 June 2014

Publication Date:
16 July 2014 (online)


Abstract

A new straightforward approach to 3-indolyl-derived cyclopenta[b]indoles by a Lewis acid triggered [3+2] cyclodimerization of 2-(3-indolyl)cyclopropane-1,1-dicarboxylic acid diesters was developed. This reaction exhibits exceptional chemo-, regio-, and diastereoselectivities, leading to the formation of an individual diastereomer with a relative configuration that corresponds to that of naturally occurring indole terpenoids.

Supporting Information

 
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