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

Olga A. Ivanova; Ekaterina M. Budynina; Dmitriy A. Skvortsov; Igor V. Trushkov; Mikhail Ya. Melnikov

doi:10.1055/s-0034-1378372

Synlett, Inhaltsverzeichnis

Synlett 2014; 25(16): 2289-2292
DOI: 10.1055/s-0034-1378372

cluster

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

Olga A. Ivanova

^aDepartment 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*

^aDepartment 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

^bLaboratory of Chemical Synthesis, Federal Research Center of Pediatric Hematology, Oncology, and Immunology, Samory Mashela. 1, Moscow 117997, Russian Federation

,

Dmitriy A. Skvortsov

^aDepartment 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

^aDepartment 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

^bLaboratory of Chemical Synthesis, Federal Research Center of Pediatric Hematology, Oncology, and Immunology, Samory Mashela. 1, Moscow 117997, Russian Federation

,

Mikhail Ya. Melnikov

^aDepartment 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

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Abstract

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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.

Key words

annulations - dimerizations - fused-ring systems - indoles - regioselectivity - stereoselectivity

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Referenzen

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