Synthesis of Hydrolytically Stable TBDMS Derivatives of Hydroxynaphthoquinones

摘要

Numerous organosilicon compounds have been shown to possess potent biological activity. Silyl derivatives of the well-known bioactive hydroxyquinones are expected to be also highly bioactive. Within our continuing interest in the silylation reaction of quinones, we recently reported on the trimethylsilylation of hydroxyquinones. Since, sterically crowed TBDMS ethers were found to be much more stable than the hydrolytically unstable TMS ethers, we were prompted to study tert-butyldimethylsilylation of hydroxynaphthoquinones on which we hereby report. The silylation is achieved by a general, clear, and one-step process.