Reaction of levoglucosenone with (±)-α-terpineol and its acetate

Reaction of levoglucosenone with Dane’s diene

“…Cycloadditions of levoglucosenone (1) to 1,3-dienes provide a convenient synthetic route to optically active cyclohexene derivatives, and they follow general rules established for Diels-Alder reactions [1][2][3][4][5][6][7][8][9][10]. With the goal of elucidating the possibility of using levoglucosenone (1) as chiral inductor in the synthesis of steroids and obtaining an estrone analog containing a carbohydrate fragment instead of the D ring, in the present work we studied the reaction of levoglucosenone (1) with Dane's diene (7-methoxy-4-vinyl-1,2dihydronaphthalene).…”