Functionalized Cycloheptanes from Bicyclo[4.2.1]nonanes

Several oxidative, reductive and C,C‐cleavage reactions were performed starting from the three bicyclo[4.2.1]nona‐3,7‐diene‐2‐one derivatives 1, 5 and 18 . The oxidations were selective and led to the diols 2,8 and 9 , and the epoxides 6,9 , and 20 . The reductions were selective only in the case of 20 21 ; otherwise they led to mixtures of the alcohols 10 and 11 , and of the dienes 14 and 15 . The periodate ring cleavages afforded the functionalized cycloheptane derivatives 3, 12, 13 and 16 . Configurational assignments were made on the basis of detailed 1 H‐NMR and X‐ray analysis of 20 .