Rin -Opening of Acetal III (8,13/13,17-Diepoxy-14,15-dinorlabdane) and the Synthesis of Potential Odorants Derived From Manool

Abstract

A novel ring opening of the acetal III (2) (8,13:13,17-diepoxy-14,15-dinorlabdane) with boron trifluoride/acetic anhydride led to the synthesis of acetals (16), (18)-(20) and (25)-(27) functionalized at C 12. The attempted ring opening of the hydroxy acetal (28) produced the dimer (32). Also prepared were the cyclic ethers (36), (38) and (39), none of which, however, exhibited significant ambergris-type odours.