The California red scale sex pheromone, produced by one of the most significant citrus pests, was originally identified in 1977 by Gieselmann and co-workers and is used by the females to attract males. Its synthesis has applications to the agricultural industry as a replacement for virgin female traps in monitoring the pest's population. Strategically, a synthesis was envisioned that leveraged a β-iodo-enoate as a lynchpin fragment capable of forging 3 key C-C bonds off the central two carbon linker. This concept was realized by first cross-coupling 4-pentenoic acid with methyl (E)-3-iodoacrylate in 54% yield, followed by a conjugate addition and saponification in 80% and 86% respectively to provide acid 28. The synthesis could be completed by coupling 28 and acetate 29, however, upon generation of the primary radical under the reaction conditions, it would undergo a 5-exo-trig cyclization before cross-coupling of the vinyl iodide could take place. This problem was obviated by increasing the catalyst loading to 40 mol% to provide California red scale pheromone in 56% yield and six steps LLS. The importance of the homologated terpene (E,E)-homofarnesol (30) stems from its use as a cyclization precursor to the vital terpene Ambrox ® (ambroxide)-a molecule with a storied history dating back to the 15 th century. Many of the reported syntheses of 30 rely on [2,3] rearrangements of the nerolidols that lead to mixtures of E/Z isomers which, if not carefully separated, give complex mixtures of cyclization products that harm its fragrant properties. In contrast, acid 31 (readily prepared from geranyl bromide and diethyl malonate) was in situ activated and coupled with vinyl iodide 32 bearing a free alcohol to arrive directly at (E,E)homofarnesol (>4 grams prepared in single pass).