A formal, one-pot β-chlorination of primary alcohols and its utilization in the transformation of terpene feedstock and the synthesis of a C 2-symmetrical terminal bis-epoxide

Abstract

A one-pot transformation of alkan-1-ols into 2-chloroalkan-1-ols is described. As a practical application, terpene-derived primary alcohols were converted into semiochemicals such as olfactory lactones (aerangis lactone, whisky lactone, and cognac lactone) and pheromones (cruentol and ferrugineol). Using heptane-1,7-diol as a bifunctional substrate, the corresponding bis-epoxide was synthesized by bidirectional synthesis in good yield and high enantioselectivity. © 2014 American Chemical Society.