title: SmI2-mediated cross-coupling of nitrones with β-silyl acrylates: synthesis of (+)-australine.
abstract: The SmI(2)-mediated cross-coupling of nitrones with β-silyl-α,β-unsaturated esters, followed by zinc reduction, allows an efficient and highly diastereoselective preparation of β-silyl lactams, which are precursors of β-hydroxy lactams through Tamao-Fleming oxidation. By applying the method to a cyclic, carbohydrate-derived nitrone, a new synthesis of (+)-australine has been realized in only 11 steps and in 21% overall yield from L-xylose.
authors.affiliation: Département de Chimie Moléculaire (SERCO) UMR-5250, ICMG FR-2607, CNRS, Université Joseph Fourier, BP 53, 38041 Grenoble Cedex 09, France.
authors.forename: Pierre
authors.initials: P
authors.lastname: Gilles
authors.forename: Sandrine
authors.initials: S
authors.lastname: Py
mesh_terms: D000179:Acrylates / Q000737:chemistry*; D007454:Iodides / Q000737:chemistry*; D015394:Molecular Structure; D009589:Nitrogen Oxides / Q000737:chemistry*; D010084:Oxidation-Reduction; D011763:Pyrrolizidine Alkaloids / Q000138:chemical synthesis*; D012493:Samarium / Q000737:chemistry*; D013237:Stereoisomerism; D015032:Zinc / Q000737:chemistry
chemical_list: D000179:Acrylates; D007454:Iodides; D009589:Nitrogen Oxides; D011763:Pyrrolizidine Alkaloids; C015388:nitrones; C059794:australine; D012493:Samarium; D015032:Zinc; C409809:samarium diiodide