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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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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

Natural Products

Opium Poppy

Penicillum Fungi

Chromodorismacfarlandi

Morphine

Penicillin

Macfarlandin E


Diaryl ether heptanoids

Diaryl Ether Heptanoids

  • Exhibit useful biological activities

    • Anti-inflammatory

    • Anticancer

    • Antibacterial

  • General structure

    • Seven carbon chain tethered

      together by a diaryl ether

      linkage

    • Cyclophanes


Optical activity

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

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Question

Question

  • These compounds are almost identical to each other

    • Minimal difference in substituents

    • Why such a difference in optical rotation?


Isolation

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


Hypothesis

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


Enantioselectivity

Enantioselectivity

  • Selective synthesis of one enantiomer

  • Pathway

    • Cu catalyst on non-racemic, chiralligands promotes the enantioselective synthesis of 9’-desmethylgarugamblin I


Chiral catalysts

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


Mechanistic considerations

Mechanistic Considerations


Progress

Progress


Future research

Future Research

  • Enantioselective synthesis of other aryl ethers


Acknowledgements

Acknowledgements

  • Howard Hughes Medical Institute

  • Undergraduate Research, Innovation, Scholarship, & Creativity (URISC) Program

  • Dr. Christopher M. Beaudry

  • Dr. Kevin Ahern


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