No abstract

Synthesis of title compounds based on adamantane and 8-oxabicyclo[3.2.1]octane scaffolds and evaluation of their biological activity.

The first directed synthesis of seven‐membered mono‐ and tris‐phosphates is described. The key steps involve a DIBAL‐H/DIBAL‐Cl‐mediated ring opening of 8‐oxabicyclo[3.2.1]octenes in the presence of [Ni(acac)2] and stereoselective syn‐dihydroxylation with NMO and OsO4. An enantioselective approach to ring opening has been examined with chiral phosphane. The phosphorylation of mono‐ and triols followed by deprotection gave the corresponding phosphates in high yields with structures similar to those of known inhibitors of myo‐inositol monophosphatase (IMPase) and myo‐inositol tris‐phosphate receptor ligands. The inhibitory activities of the monophosphates thus formed were evaluated against IMPase.