Synthetic Studies on Anticancer Compounds: The Tylophorinines

This thesis describes synthetic studies in the area of alkaloid chemistry, specifically, potent anticancer compounds: the tylophorinines.

Tylophorinine is a naturally occurring compound found in the Monarch butterfly and plants of the genus Tylophora. Described here is a concise methodology for stereoselective synthesis of this compound, and analogs, starting from simple, naturally occurring compounds. The synthetic strategy represents a simplification in synthesizing tylophorinines, and would allow numerous other tylophorinines with similar chemical structure to be conveniently synthesized in an analogous fashion.

Further, the tylophorinines are convenient compounds for determining where a cancer cell may be most effectively attacked. Numerous attempts were made to alkylate and then biotinylate a tylophorinine, in the hopes that a cancer protein would be snared, leading to the determination of the tylophorinines mode of action in the cancer cell.