A five-step synthesis of muscone, a molecule with commercial and cultural relevance, has been developed for an advanced organic chemistry lab to correlate with classroom learning objectives, to train students to effectively conduct synthetic chemistry experiments, and to provide students with greater context for organic chemistry’s relevance.  The synthesis is completed over the course of a semester and progresses parallel to topics taught in a traditional second semester organic chemistry course.  The sequence of reactions illustrates functional group inter-conversion (alcohol to alkyl bromide), carbonyl chemistry (Grignard reaction), oxidation (pyridinium chlorochromate), carbon bond formation (ring closing metathesis), and reduction (hydrogenation).  Along with conducting the total synthesis, learning activities ensure that students properly maintain a lab notebook; employ literature precedent to scale, setup, and execute reactions; explore muscone’s relevance in other fields of study; and use <sup>1</sup>H and <sup>13</sup>C NMR as well as GCMS and IR to verify and report structure.

Total synthesis of muscone for the advanced organic chemistry lab

256th National Meeting (2018)

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