Carbanion chemistry represents an enormously important set of reactions in the organic chemist‘s arsenal, as exemplified in the total synthesis of bongkrekic acid (above), a potential apoptosis inhibitor, which involves asymmetric alkylation and anionic allyl coupling (Shindo, M.; Sugioka, T.; Umaba, Y.; Shishido, K. Tetrahedron Lett. 2004, 45, 8863).

This advanced course examines the use of carbanion techniques in total synthesis and synthetic methodology from the current literature. Related topics are also considered, such as protection/deprotection technology, stereoelectronic considerations, and other key steps in the synthetic plans.

Students contribute to the class through literature research, discussion, and in-class presentations. Credit: Two semester hours. Taught second half of the semester.

Prerequisite: Chem 232.