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

2013 cs

Izgu, E. C.; Hoye, T. R. Chem. Sci. 2013, 4, 2262–2266

Highlighted in Synfacts 2013, 9, 589. (DOI: 10.1005/s-0033-1338715)

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.