Formal Total Synthesis of Platencin

The right bicycle: A concise formal synthesis of platencin was based on an efficient oxygen-mediated palladium-catalyzed cycloalkenylation of 1 to form a bicyclo[3.2.1]octane, and a deoxygenative rearrangement of tosylhydrazone 2 to construct the bicyclo[2.2.2]octane 3. The total yield of the core structure 4 of platencin was 17.5% for 13 steps from a commercially available compound. Ts = p-toluenesulfonyl, TBS = tert-butyldimethylsilyl, Piv = pivaloyl.