Issue 98, 2013
From the journal:

Chemical Communications

A bioinspired route to indanes and cyclopentannulated hetarenes via (3+2)-cyclodimerization of donor–acceptor cyclopropanes†

Olga A. Ivanova,a   Ekaterina M. Budynina,*ab   Dmitriy A. Skvortsov,a   Michelle Limoge,c   Andrei V. Bakin,c   Alexey O. Chagarovskiy,ab   Igor V. Trushkovab  and  Mikhail Ya. Melnikova  

* Corresponding authors

a M.V. Lomonosov Moscow State University, Department of Chemistry, Leninskie Gory, 1-3, 119991 Moscow, Russia
E-mail: ekatbud@kinet.chem.msu.ru
Fax: +7 495 9391814
Tel: +7 495 9391316

b Federal Research Center of Pediatric Hematology, Oncology and Immunology, Laboratory of Chemical Synthesis, ul. Samory Mashela 1, Moscow 117997, Russia

c Department of Cancer Genetics, Roswell Park Cancer Institute, Elm and Carlton Sts., Buffalo, NY 14263, USA

Abstract

A novel Lewis acid-catalyzed domino (3+2)-cyclodimerization of 2-arylcyclopropane-1,1-diesters and related stepwise cross-reaction of two different cyclopropanes were developed. These processes provide efficient and highly stereoselective access to polyoxygenated indanes and cyclopentannulated heteroarene derivatives, which display significant cytotoxicity against several lines of cancer cells (IC50 of 10−6–10−5 M) while being non-toxic for normal cells.

Graphical abstract: A bioinspired route to indanes and cyclopentannulated hetarenes via (3+2)-cyclodimerization of donor–acceptor cyclopropanes

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Article information

DOI
https://doi.org/10.1039/C3CC44475A
Article type
Communication
Submitted
14 Jun 2013
Accepted
03 Jul 2013
First published
04 Jul 2013

Chem. Commun., 2013,49, 11482-11484

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A bioinspired route to indanes and cyclopentannulated hetarenes via (3+2)-cyclodimerization of donor–acceptor cyclopropanes

O. A. Ivanova, E. M. Budynina, D. A. Skvortsov, M. Limoge, A. V. Bakin, A. O. Chagarovskiy, I. V. Trushkov and M. Ya. Melnikov, Chem. Commun., 2013, 49, 11482 DOI: 10.1039/C3CC44475A

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