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Issue 5, 2013
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Total synthesis of (±)-leuconolam: intramolecular allylic silane addition to a maleimide carbonyl group

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Abstract

A concise total synthesis of the plant alkaloid (±)-leuconolam (1) has been achieved. A regio- and diastereoselective Lewis-acid mediated allylative cyclization was used to establish, simultaneously, two adjacent tetrasubstituted carbon centers. Furthermore, an essential arene cross-coupling to a hindered haloalkene was enabled by the use of a novel 2-anilinostannane.

Graphical abstract: Total synthesis of (±)-leuconolam: intramolecular allylic silane addition to a maleimide carbonyl group

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Publication details

The article was received on 08 Jan 2013, accepted on 13 Mar 2013 and first published on 14 Mar 2013


Article type: Edge Article
DOI: 10.1039/C3SC00056G
Citation: Chem. Sci., 2013,4, 2262-2266
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    Total synthesis of (±)-leuconolam: intramolecular allylic silane addition to a maleimide carbonyl group

    E. C. Izgu and T. R. Hoye, Chem. Sci., 2013, 4, 2262
    DOI: 10.1039/C3SC00056G

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