Oxidative degradations of the side chain of unsaturated Ent-labdanes. Part II

Abstract

A route for the degradation of the side chain of ent-labdane derivatives has been devised, giving the useful synthon 2β,12-dihydroxy-13,14,15,16,17- pentanor-ent-labdane-8-one (8). The use of this compound in the preparation of terpenylquinone derivatives shall be reported elsewhere. In addition we have synthesized the compound 2β,12-diacetoxy-8β,17-epoxy-13,14,15,16- tetranor-ent-labdane (10), which upon catalytic epoxide ring opening in alkaline or acid media gave rise in all cases to the formation of tricyclic compounds. © 2007 by MDPI.