3 years ago

Vinyl Grignard-Mediated Stereoselective Carbocyclization of Lactone Acetals

Vinyl Grignard-Mediated
Stereoselective Carbocyclization
of Lactone Acetals
Morten Estrup, Henrik H. Jensen, Christinne Hedberg, Espen Z. Eikeland
A novel Ferrier-type carbocyclization is reported. It involves a carbohydrate-derived lactone acetal synthesized from methyl α-d-glucopyranoside, which upon treatment with excess vinylmagnesium bromide provides a highly substituted carbocyclic product as a single stereoisomer. The yield is greatly increased when N,N,N′,N′-tetramethylethylenediamine is added to the reaction mixture. Optimized reaction conditions have been applied to lactone acetals derived from other carbohydrates. Based on the obtained results, a possible reaction mechanism has been proposed. Furthermore, scalability of the reaction up to 15 g scale and derivatization of the carbocyclic product has been demonstrated, including the formation of a rare trans-bicyclo[4.3.0]nonene scaffold via a ring-closing metathesis. The structure of this and all carbocyclic products were confirmed by X-ray crystallographic analysis.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b03079

DOI: 10.1021/acs.joc.7b03079

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