The chemical synthesis of structurally and stereochemically complex molecules is a focal point of the pharmaceutical, agricultural, and materials industries.  To optimize the desired parameters affiliated with their syntheses (step, atom, redox economies), we rely heavily upon the discovery of catalysts that can accomplish early- and late-stage bond construction under mild conditions, broad functional group tolerance, and with little to no waste production.  This seminar will feature a combination of chemical and enzymatic strategies for achieving catalytic carbon-carbon (C-C) bond formation.  It will be divided into three parts including 1) the development of an organocatalytic hydroxymethylation protocol and its application in the total synthesis of the apoptosis inducer, (-)-rasfonin, 2) photoexcitation of flavoenzymes for stereoselective C-C bond formation, and 3) the development of a class of terpene cyclases using oxyanion hole catalysis in hydrolase enzymes.