Faculty Advisor

Dittami, James P.

Abstract

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 should produce a compound with compelling biological activity from a brief, diversifiable synthesis.

Publisher

Worcester Polytechnic Institute

Date Accepted

April 2009

Major

Chemistry

Project Type

Major Qualifying Project

Accessibility

Unrestricted

Advisor Department

Chemistry and Biochemistry

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