Kiyoharu Nishide

Regioselective ring opening of unsymmetrical cyclic ethers with the A1C13-NaI-acetonitrile system: Application to hydroxylation of ent-kaurene.

Abstract Unsymmetrically substituted 5-membered cyclic ethers were effectively cleaved with the A1C1 3 -NaI-CH 3 CN system at the less hindered carbon atom to afford δ-iodoalcohols. Conversion of ent -kaurene to ent -14α- and ent -12β-hydroxykaurene was achieved through the ring opening of the cyclic ether with the present system as a key step.

A convenient reduction of functionalized polycyclic aromatics into parent hydrocarbons

Abstract Polycyclic aromatics with various functional group (e.g. OH, OR, SR, and halogen) were easily defunctionalized by aluminum chloride and ethanethiol to give parent aromatics in high yields under mild conditions. This reaction proceeds through sulfide as the intermediate, hence it is also useful for the synthesis of sulfides of polycyclic aromatics.