Lewis acid catalyzed cyclization and coupling reactions to synthesize compounds of biological interests

This research includes four parts: (1) synthesis of tetrahydropyran derivatives, (2) novel alkyne-aldehyde coupling reaction and a novel alkyne-alcohol cyclization reaction, (3) synthesis of polysubstituted naphthalene derivatives and (4) synthetic studies directed toward Epicalyxin F.; Part one. Synthesis of tetrahydropyran derivatives. Various Lewis acids mediate the cyclization between homoallylic alcohols and aldehydes to generate 4-chlorotetrahydropyans and 4-hydroxytetrahydropyrans.; Part two. Novel alkyne-aldehyde coupling reaction and a novel alkyne-alcohol cyclization reaction. Gallium trichloride catalyzed cyclization between alkynes and aldehydes to generate unsaturated ketones and five membered indenes. Also, gallium trichloride catalyzed a novel, unusual cyclization between alkynes and allyl alcohols to generate a very interesting 5 membered ring system.; Part three. Synthesis of polysubstituted naphthalene derivatives . Polysubstituted naphthalene derivatives were conveniently synthesized via a gallium trichloride catalyzed cyclization between aromatic alkynes and phenyl aldehydes and ketones.; Part four. Synthetic studies of Epicalyxin F. Studies are currently underway to synthesize Epicalyxin F, a natural product based on the various Lewis acid promoted couplings and cyclization reactions discovered in our laboratory.