Amaryllidaceae isoquinoline alkaloids as well as their analogs have long been of interest as lead compounds in drug discovery due to their range of biological activity. Many of these alkaloids are cytotoxic anti-tumor agents. Moreover, there have also been studies showing<br/>the effectiveness of these molecules against yellow fever and other diseases caused by RNA containing flaviviruses. The study of these compounds as pharmaceutical agents is hampered by their low natural abundance, which necessitates the development of laboratory<br/>syntheses of these alkaloids and their analogs.<br/>This project focuses on the total syntheses of the Pancratistatin-type natural products that contain the phenanthridone ring system. In stage one, model systems are being investigated to develop the methodology required to introduce requisite functionality found in natural systems. Previous research from this laboratory gives the basic phenanthridone skeleton with several different functional groups, but there are no reported methods for converting these functions into polyhydroxycyclohexanes with stereochemical control. Two of the problems under investigation involve the oxidations of alkenes to make diols and reducing tetrasubstituted double bonds with control of stereochemistry. In stage two, a specific phenanthridone alkaloid will be targeted for total synthesis that uses the new methodology developed in stage one.

Steps towards the novel synthesis of pancratistatin-type analogs

255th National Meeting (2018)

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