Thesis advisor: Amir H. Hoveyda / We have devised a broadly applicable catalytic cross-metathesis method for stereoretentive synthesis of Z- and E-trisubstituted α,β-unsaturated esters. Several new Mo-bisaryloxide complexes were prepared, and they showed superior efficiency in synthesizing the Z-trisubstituted enoates (vs. corresponding mono-aryloxide pyrrolide complexes). Synthetic utility of the method was demonstrated through several concise syntheses of bioactive triterpenoids and value-added derivatives of prenyl-containing compounds such as citronellal, citronellol, and geraniol, all of which are isolated from essential oils. This transformation offers a valuable alternative to carbonyl olefination approaches such as Wittig and Horner-Wadsworth-Emmons reactions. / Thesis (MS) — Boston College, 2021. / Submitted to: Boston College. Graduate School of Arts and Sciences. / Discipline: Chemistry.