The results of investigations carried out over a three year period in the Laboratory of Hydrocarbon Chemistry of the Institute of Petrochemical Synthesis of the Russian Academy of Sciences in the field of the activation and mild functionalization of adamantane, alkyladamantanes and adamantanones are generalized. It is shown that a number of catalytic systems (polyoxometallates, metalloporphyrins, modified Gif-systems) are capable of carrying out the oxidation of adamantane, 1,3-dimethyladamantane (1,3-DMA) and other alkyladamantanes to alcohols and ketones under mild conditions. The biotransformation of adamantane and alkyladamantanes leads to the formation solely of tertiary alcohols. As a result of biotransformation by means of strain Pseudomonas aeruginosa Bs-315 CAM, adamantanones undergo transformations, chiefly by the Bayer-Williger reaction, with the formation of the corresponding lactones. At the same time, problems of selectivity in the oxidation of adamantanes and oxidation by the alkyl, in particular methyl, groups of alkyladamantanes remain unresolved.