Synthesis of a caryophyllene isoprenologue, a potential diterpene natural product

(−)-β-Caryophyllene has been converted into three stereoisomers of a new bicyclic compound that is structurally related to the known macrocyclic diterpene, flexibilene, in the same way β-caryophyllene is related to humulene. Key steps are selective cleavage of caryophyllene, addition of a five carbon component by a Wittig reaction and McMurry cyclization.