Phosphates of bridgehead alcohols as putative inositol monophosphatase inhibitors: molecular design and synthetic approach

To enhance the lipophilicity of d-3,5,6-trideoxyinositol monophosphate, the IMPase inhibitor, its bridgehead analogues were suggested on the basis of molecular modeling. Adamantane-1,2- and 1,4-diols were converted into their 1-phosphates via the step of benzylic protection of the secondary hydroxy groups; the Baeyer–Villiger oxidation of 1-hydroxyadamantan-2-one occurred to initially cleave C(1)–C(2) bond.