Issue 98, 2013

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

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

Supplementary files

Article information

Article type
Communication
Submitted
14 Jun 2013
Accepted
03 Jul 2013
First published
04 Jul 2013

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

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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