Stereospecific synthesis of (Z,Z,Z,Z,Z,Z,Z,Z,E,E)-undecaprenol (bacterialprenol) using an all-cis-diterpene building block

Abstract

Base-induced coupling of two monoterpene building blocks (6) and (7) followed by functional group transformations afforded an all-cis-diterpene building block (4), which was used to effect C₂₀ homologation of (E,E)-farnesol and (Z,Z,Z,Z,E,E)-heptaprenol (betulaprenol-7)(9)via the corresponding p-tolyl sulphones; thus the title undecaprenol (1) was synthesised stereospecifically in short steps.