Synthesis of a Novel Multicyclic Organic Scaffold via a Photoinitiated Intramolecular Ylide-Alkene Cycloaddition Reaction

Costa, Brian C.

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Synthesis of a Novel Multicyclic Organic Scaffold via a Photoinitiated Intramolecular Ylide-Alkene Cycloaddition Reaction

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Access to a diverse array of druglike organic molecules via efficient total synthesis is of critical importance for the exploration of new compounds of biological and medicinal interest. In particular, any viable synthetic route to such molecules must incorporate precise control of stereochemistry as well as the ability to tune medicinally relevant parameters. Synthesis of a bioisosteric analog of the opiate analgesic morphine was pursued using an intramolecular ylide-alkene cycloaddition as the key step which would establish the configuration of the six stereocenters of the molecule in a single operation. The novel structure of the target analog is expected to produce a compound with compelling biological activity from a brief, diversifiable synthesis.

This report represents the work of one or more WPI undergraduate students submitted to the faculty as evidence of completion of a degree requirement. WPI routinely publishes these reports on its website without editorial or peer review.

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