Nitrones and oxaziridines. XXXIII. Synthesis of bridgehead-hydroxylated bicyclic 1-pyrroline 1-oxides

Abstract

The α-hydroxy-γ-nitro ketones (3), (9, (7) and (10) have been prepared from the respective γ-nitro ketones (1), (4), (6) and (9) by a sequence involving formation and epoxidation of the intermediate enol acetate, and hydrolysis of the epoxide. Reductive cyclization of the α-hydroxy-γ-nitro ketones (3), (7) and (10) gave the bridgehead-hydroxylated nitrones (ll), (12) and (13) respectively.