REGIOSELECTIVE RING OPENING OF UNSYMMETRICAL CYCLIC ETHERS WITH THE AlCl3-NaI-ACETONITRILE SYSTEM: APPLICATION TO HYDROXYLATION OF ent-KAURENE.

Article abstract of DOI:10.1016/S0040-4039(00)99844-7

Unsymmetrically substituted 5-membered cyclic ethers were effectively cleaved with the AlCl3-NaI-CH3CN 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 t