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A Model System For A Diazine-Benzofuran Cycloaddition/Fragmentation Approach To Thebaine

A Model System For A Diazine-Benzofuran Cycloaddition/Fragmentation Approach To Thebaine. Alex Hadduck Member of the Paul Blakemore Research Group 2006. Why Thebaine?.

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A Model System For A Diazine-Benzofuran Cycloaddition/Fragmentation Approach To Thebaine

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  1. A Model System For A Diazine-Benzofuran Cycloaddition/Fragmentation Approach To Thebaine Alex Hadduck Member of the Paul Blakemore Research Group 2006

  2. Why Thebaine? • Not medicinally used, but the precursor to many opiates including morphine, codeine, heroin, and dozens of other tranquilizers (such as the elephant tranquilizer Etorphine). • Current opiate synthesis requires dozens of steps with low yields, nowhere near the efficiency of harvesting raw poppy • Political instability in Asia Minor, the primary source of natural poppy, makes natural poppy production unreliable

  3. Thebaine

  4. Codeine • *Analgesic, antitussive, antidiarrheal

  5. Morphine • Severe pain relief – trauma, surgery, cancer.

  6. Diamorphine (aka heroin) • Still used in hospitals – acute pain

  7. Ethics • “All opiod analgesics cause dependence and tolerance, but that is no deterrent in the control of pain in terminal illness.” -British National Formulary • Federal regulations and laboratory integrity

  8. Goals and reasoning • Create 14 carbon morphinan skeleton • Coax the skeleton into a cycloaddition, creating a thebaine analogue • Using a model system allows to test the basic theories involved in the envisioned synthesis without extra hindrance. No controlled substances! • Target synthesis = trial and error

  9. Overall Scheme

  10. Reactions thus far

  11. Reactions thus far cont.

  12. The rest of the summer and beyond • Joining of the benzofuran and pyridazine • Closure of the morphinan skelton • Future work

  13. Thanks • Howard Hughes Medical Institute • Paul Blakemore • Selena Milicevic • Mark Sephton • Kevin Ahern and Indira Rajagopal

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