Concise approach to pyrrolizino[1,2-b]indoles from indole-derived donor–acceptor cyclopropanes

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

doi:10.1039/C6RA11233A

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Concise approach to pyrrolizino[1,2-b]indoles from indole-derived donor–acceptor cyclopropanes†

Elena V. Villemson,^ab Ekaterina M. Budynina,^a Olga A. Ivanova,^ab Dmitriy A. Skvortsov,^ab Igor V. Trushkov*^ab and Mikhail Ya. Melnikov^a

Author affiliations

* Corresponding authors

^a Department of Chemistry, M. V. Lomonosov Moscow State University, Leninskie Gory, 1-3, Moscow, Russian Federation 119991
E-mail: itrushkov@mail.ru

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

Abstract

Developed here is a direct three-step approach to a previously unexplored pyrrolizino[1,2-b]indole system based on a sequence of three synthetic steps: (a) one-pot azide ion promoted ring opening of the indole-derived donor–acceptor cyclopropane and Krapcho dealkoxycarbonylation; (b) Vilsmeier–Haack formylation; (c) tandem Staudinger/intramolecular aza-Wittig reaction and reductive cyclization realized in a one pot fashion.

This article is part of the themed collection: Elegant Synthetic Routes to Indole Derivatives

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Article information

DOI: https://doi.org/10.1039/C6RA11233A
Article type: Communication
Submitted: 30 Apr 2016
Accepted: 21 Jun 2016
First published: 23 Jun 2016

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RSC Adv., 2016,6, 62014-62018

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Concise approach to pyrrolizino[1,2-b]indoles from indole-derived donor–acceptor cyclopropanes

E. V. Villemson, E. M. Budynina, O. A. Ivanova, D. A. Skvortsov, I. V. Trushkov and M. Ya. Melnikov, RSC Adv., 2016, 6, 62014 DOI: 10.1039/C6RA11233A

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Concise approach to pyrrolizino[1,2-b]indoles from indole-derived donor–acceptor cyclopropanes†

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Concise approach to pyrrolizino[1,2-b]indoles from indole-derived donor–acceptor cyclopropanes

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