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

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 hi...

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Bibliographic Details
Published in:Chemical science (Cambridge) 2013-02, Vol.4 (5), p.2262-2266
Main Authors: Izgu, Enver Cagri, Hoye, Thomas R
Format: Article
Language:English
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Summary: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.
ISSN:2041-6520
2041-6539
DOI:10.1039/c3sc00056g