Dittami, James P.
This project investigated the feasibility of synthesizing the tetracyclic ergotamine backbone by way of an intramolecular ylide alkene [3+2] cycloaddition from aryl vinyl ether 9 to addition product 8. Photolysis reactions of photoprecursors 9 and 30 did not yield the anticipated products but rather the structures 42, 44 and 41 respectively. At present these systems do not appear to be useful in the synthesis of ergot derivatives, but do appear to have applications in synthesizing diazepines and norepinephrine reuptake inhibitors.
Worcester Polytechnic Institute
Major Qualifying Project
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Chemistry and Biochemistry