Benzoylation of ergosterol through nucleophilic acyl substitution and subsequent formation of ergosterol benzoate endoperoxide by reaction with singlet oxygen generated by photosensitization

摘要

A multifaceted procedure is provided that correlates well with introductory organic chemistry or upper-level mechanistic chemistry. Lecture topics including carboxylic acid chemistry, the Diels-Alder reaction, photochemistry, and UV-vis and NMR spectroscopy are reinforced and the student is provided the opportunity to become more adept with laboratory procedures, in particular, TLC and column chromatography. The student will also gain exposure to topics that he or she will see in future courses such as ROS, steroid structures, and aspects of vitamin D chemistry.