info:eu-repo/semantics/article
Asymmetric synthesis of: Trans -4,5-disubstituted γ-butyrolactones involving a key allylboration step. First access to (-)-nicotlactone B and (-)-galbacin
Fecha
2018-02Registro en:
Henrion, S.; Macé, A.; Vallejos, Margarita; Roisnel, T.; Carboni, B.; et al.; Asymmetric synthesis of: Trans -4,5-disubstituted γ-butyrolactones involving a key allylboration step. First access to (-)-nicotlactone B and (-)-galbacin; Royal Society of Chemistry; Organic & Biomolecular Chemistry; 16; 10; 2-2018; 1672-1678
1477-0520
CONICET Digital
CONICET
Autor
Henrion, S.
Macé, A.
Vallejos, Margarita
Roisnel, T.
Carboni, B.
Villalgordo, J.M.
Carreaux, Francois
Resumen
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.