Synthesis of isovalerenenol, a sesquiterpene alcohol isolated from a soft coral and the stability of related hydrindanone derivatives

Article abstract of DOI:10.1016/0040-4020(96)00544-3

Isovalerenenol (2) was synthesized using intramolecular aldol and hydrogenation reactions of the corresponding hydrindenone derivative. The hydrogenation afforded exclusively one desired product, while the other isomer gave several products, whose structures were determined by spectroscopic methods as well as base treatments. The introduction of α,β-unsaturated aldehyde was accomplished by the Grignard reaction using vinyl magnesium bromide and oxidative allyl alcohol rearrangement.