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Synlett 2011(5): 589-593  
DOI: 10.1055/s-0030-1259553
SYNPACTS
© Georg Thieme Verlag Stuttgart ˙ New York

Cyclization of Aminocyclopropanes in Indole Alkaloids Synthesis

Filippo De Simone, Jérôme Waser*
Laboratory of Catalysis and Organic Synthesis, Ecole Polytechnique Fédérale de Lausanne, EPFL SB ISIC LCSO BCH 4306, 1015 Lausanne, Switzerland
Fax: +41(21)6939700; e-Mail: jerome.waser@epfl.ch;
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Publication History

Received 9 December 2010
Publication Date:
11 February 2011 (online)

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Abstract

The regioselective and diastereoselective cyclization of acyliminium intermediates generated from aminocyclopropanes on unprotected indoles is presented. The recent results obtained in our group are compared with previous intermolecular reactions with aminocyclopropanes as well as with other cyclization methods involving iminium ions and unprotected indoles. A first speculative analysis of possible reaction mechanisms allows rationalizing the observed selectivity. The high potential of the method for the synthesis of natural alkaloids is demonstrated in the formal synthesis of aspidospermidine and the total synthesis of goniomitine.

Key words

alkaloids - cyclization - indoles - iminium - aminocyclopropanes

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The biological assays were done in the laboratory of Prof. Jürg Gertsch at the University of Bern in the framework of a COST CM0804 (Chemical Biology with Natural Products) collaboration.