Cyclization and Rearrangements of Farnesol and Nerolidol Stereoisomers in Superacids

Article abstract of DOI:10.1021/jo00085a044

Acid-catalyzed cyclization of 2,3-trans- and 2,3-cis-farnesol proceeds regioselectively and stereospecifically, yielding drimenol and epi-drimenol, respectively.The trans and cis isomers of nerolidol undergo carbo- and heterocyclization reactions.The trans isomer gives tricyclic caged hydrocarbons with new skeletal types, while the rearrangements of the cis isomer produce derivatives of 2-oxabicyclo<4.4.0>decane.The ICAR computer program was used to derive reasonable mechanisms for the acid-catalyzed transformations of nerolidol, and the probability of the mechanisms was evaluated by the molecular mechanics method.