Total Synthesis of (±)-Cameroonanol

[GRAPHICS] The structure and relative stereochemistry of the novel silphiperfolane-type sesquiterpene cameroonan-7 alpha-ol (1) were confirmed by a total synthesis of (+/-)-1l from 3,3,5-trimethylbicyclo[3.3.0]oct-1(8)-en-2-one (6) by means of a Sakurai reaction with (Z)-crotylsilane, free radical hydrobromination, base-induced cyclization, and LiAIH(4) reduction.