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

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.

SUBMITTER: Izgu EC

PROVIDER: S-EPMC4238231 | biostudies-literature | 2013 Feb

REPOSITORIES: biostudies-literature

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

Izgu Enver Cagri EC Hoye Thomas R TR

Chemical science 20130201 5

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. ...[more]

PMID: 25419448

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