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

Enver Cagri Izgu; Thomas R. Hoye

doi:10.1039/c3sc00056g

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

Enver Cagri Izgu, Thomas R. Hoye

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23 Scopus citations

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.

Original language	English (US)
Pages (from-to)	2262-2266
Number of pages	5
Journal	Chemical Science
Volume	4
Issue number	5
DOIs	https://doi.org/10.1039/c3sc00056g
State	Published - Apr 2 2013
Externally published	Yes

All Science Journal Classification (ASJC) codes

Chemistry(all)

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10.1039/c3sc00056g

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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.",

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

Abstract

All Science Journal Classification (ASJC) codes

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