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Enantioselective Synthesis of 9’-Desmethylgarugamblin I

Enantioselective Synthesis of 9’-Desmethylgarugamblin I. Andrew Willeford Dr. Christopher M. Beaudry Department of Chemistry HHMI 2009. Natural Products. Opium Poppy. Penicillum Fungi. Chromodoris macfarlandi. Morphine. Penicillin. Macfarlandin E.

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Enantioselective Synthesis of 9’-Desmethylgarugamblin I

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  1. Enantioselective Synthesis of 9’-Desmethylgarugamblin I Andrew Willeford Dr. Christopher M. Beaudry Department of Chemistry HHMI 2009

  2. Natural Products Opium Poppy Penicillum Fungi Chromodorismacfarlandi Morphine Penicillin Macfarlandin E

  3. Diaryl Ether Heptanoids • Exhibit useful biological activities • Anti-inflammatory • Anticancer • Antibacterial • General structure • Seven carbon chain tethered together by a diaryl ether linkage • Cyclophanes

  4. Optical Activity • 17 diaryl ether heptanoids do not possess stereocenters • Six of these 17 compounds are chiral by virtue of their tethered-ring structure and have been isolated as optically active compounds. • Planar chirality • Mobius Strip This work is licensed under a Creative Commons Attribution-Share Alike 3.0 Unported License.

  5. Question • These compounds are almost identical to each other • Minimal difference in substituents • Why such a difference in optical rotation?

  6. Isolation • All 17 compounds were isolated from plant sources • 9’-desmethylgarugamblin I is a bark extract of Garugapinnata • A frankencense • Found in Asia • Used in folk medicine • Typical isolation • Includes extraction in a Soxhlet apparatus at high temperatures

  7. Hypothesis • Isolation of these compounds have led to racemization • Enantioselective synthesis of 9’-desmethylgarugamblin I would allow verification of our hypothesis • Will offer proof of concept to enantioselectively synthesize the compounds with non-reported optical rotations

  8. Enantioselectivity • Selective synthesis of one enantiomer • Pathway • Cu catalyst on non-racemic, chiralligands promotes the enantioselective synthesis of 9’-desmethylgarugamblin I

  9. Chiral Catalysts • A catalyst with enantiomeric forms • Holds substrate in specific conformation • Lowers energy barrier for formation of one enantiomer • Examples • Walphos • Naud • Josiphos • Enzymes

  10. Mechanistic Considerations

  11. Progress

  12. Future Research • Enantioselective synthesis of other aryl ethers

  13. Acknowledgements • Howard Hughes Medical Institute • Undergraduate Research, Innovation, Scholarship, & Creativity (URISC) Program • Dr. Christopher M. Beaudry • Dr. Kevin Ahern

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