Diterpene chemistry. VII. Sulfur-containing derivatives of Labda-8(17),14-dien-13-ol (Manool)

The reactions of manool derivatives with sulfurated sodium borohydride to give sulfur-containing diterpene derivatives are reported. 13,17-Epithio-8,13-epoxy-14,15-dinorlabdane (12), the sulfur analogue of the highly odiferous compound 8,13:13,17-diepoxy-14,15 dinorlabdane (4), has been synthesized. A simple but very effective use of silver nitrate to prevent double-bond participation in an acetalization reaction is reported.