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.

• 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.

Creator

• Tripp, Jonathan Clive

Publisher

• Worcester Polytechnic Institute

Identifier

• 00D103M

Advisor

• Dittami, James P.

Year

• 2000

Date created

• 2000-01-01

Resource type

• Major Qualifying Project

Major

• Chemistry

Rights statement

• In Copyright