Asymmetric synthesis of: Trans -4,5-disubstituted γ-butyrolactones involving a key allylboration step. First access to (-)-nicotlactone B and (-)-galbacin

An efficient asymmetric synthesis of trans-4,5-disubstituted γ-butyrolactones from aldehydes and enantioenriched γ-carbamate alkenylboronates is reported. The cornerstone of this strategy is the implementation of sequential [3,3]-allyl cyanate rearrangement/allylboration/nucleophilic addition/cyclisation reactions. Diverse γ-butyrolactones such as the flavouring compounds, (+)-trans-whiskey lactone and (+)-trans-cognac lactone, as well as an advanced intermediate towards the first synthesis of natural products, (-)-nicotlactone B and (-)-galbacin, have thus been obtained.Fil: Henrion, S.. Université de Rennes I. Institut des Sciences Chimiques de Rennes; Francia. Centre National de la Recherche Scientifique; FranciaFil: Macé, A.. Université de Rennes I. Institut des Sciences Chimiques de Rennes; Francia. Centre National de la Recherche Scientifique; FranciaFil: Vallejos, Margarita. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Nordeste. Instituto de Química Básica y Aplicada del Nordeste Argentino. Universidad Nacional del Nordeste. Facultad de Ciencias Exactas Naturales y Agrimensura. Instituto de Química Básica y Aplicada del Nordeste Argentino; ArgentinaFil: Roisnel, T.. Université de Rennes I. Institut des Sciences Chimiques de Rennes; Francia. Centre National de la Recherche Scientifique; FranciaFil: Carboni, B.. Université de Rennes I. Institut des Sciences Chimiques de Rennes; FranciaFil: Villalgordo, J.M.. Parque Tecnológico de Fuente Alamo. VillaPharma Research; EspañaFil: Carreaux, Francois. Centre National de la Recherche Scientifique; Francia. Université de Rennes I. Institut des Sciences Chimiques de Rennes; Franci