Preparation of (R)-(2-cyclopentenyl)methanol and the first total synthesis of (8R,11R)-precapnelladiene

Article abstract of DOI:10.1246/bcsj.67.2880

Enantiometrically pure (R)-(2-cyclopentenyl)methanol (2) was prepared from ethyl 2-oxocyclopentanecarboxylate. Coupling of 2 with 4,4-dimethyl-3-phenylthio-2-cyclohexenone gave an enol ether, which was converted into (8R,11H)-precapnelladiene, [α](D)¹⁹ = -70.7°, in 6 steps.