The ability to perform multi-step syntheses that transform simple starting materials into products with greater complexity is an important goal of modern organic chemistry.  To facilitate the training of future synthetic chemists, multi-step syntheses developed specifically for the upper-level chemistry majors laboratory are needed.  Two such syntheses will be described.  The first synthesis, a four-step preparation of an expensive fine chemical building block from three commodity chemicals, utilizes a series of classic carbonyl transformations, including a Dieckmann-type annulation.   The second synthesis, a four-step preparation of resveratrol along multiple branching pathways, allows students to collectively complete and then comparatively evaluate multiple synthesis routes, thereby introducing them to numerous concepts in synthesis planning and optimization.

Two new multi-step syntheses for the advanced organic chemistry laboratory

243rd National Meeting (2012)

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