The first total synthesis of (±)-junicedranol based on a novel anionic [1,3] rearrangement

The racemate of junicedranol, a sesquiterpene-alcohol with a novel carbon skeleton, was prepared through a unique anionic [1,3] rearrangement of an 8-methylenebicyclo[3.2.1]oct-6-en-2-ol giving a cyclopentadiene derivative and the facial- and regioselective Diels–Alder reaction of the cyclopentadiene with a ketene equivalent leading to the junicedranol framework.