The chemistry of thujone. XIX. 1 Acid-promoted ring cleavage of thujone-derived cyclopropylcarbinols

Article abstract of DOI:10.1139/v96-194

Thujone-derived cyclopropylcarbinols can cleave via three distinct pathways: the exo cleavage, the endo cleavage, and the interesting cyclopropylcarbinyl rearrangement. Factors determining which pathway is adopted under specific conditions are discussed. A short sequence leading to synthesis of the sesquiterpene (+)-β-cyperone is described.