Enantioselective synthesis of 9 desmethylgarugamblin i
Sponsored Links
This presentation is the property of its rightful owner.
1 / 13

Enantioselective Synthesis of 9’-Desmethylgarugamblin I PowerPoint PPT Presentation


  • 112 Views
  • Uploaded on
  • Presentation posted in: General

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.

Download Presentation

Enantioselective Synthesis of 9’-Desmethylgarugamblin I

An Image/Link below is provided (as is) to download presentation

Download Policy: Content on the Website is provided to you AS IS for your information and personal use and may not be sold / licensed / shared on other websites without getting consent from its author.While downloading, if for some reason you are not able to download a presentation, the publisher may have deleted the file from their server.


- - - - - - - - - - - - - - - - - - - - - - - - - - E N D - - - - - - - - - - - - - - - - - - - - - - - - - -

Presentation Transcript


Enantioselective Synthesis of 9’-Desmethylgarugamblin I

Andrew Willeford

Dr. Christopher M. Beaudry

Department of Chemistry

HHMI 2009


Natural Products

Opium Poppy

Penicillum Fungi

Chromodorismacfarlandi

Morphine

Penicillin

Macfarlandin E


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

  • 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.


Question

  • These compounds are almost identical to each other

    • Minimal difference in substituents

    • Why such a difference in optical rotation?


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

  • 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

  • Selective synthesis of one enantiomer

  • Pathway

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


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


Progress


Future Research

  • Enantioselective synthesis of other aryl ethers


Acknowledgements

  • Howard Hughes Medical Institute

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

  • Dr. Christopher M. Beaudry

  • Dr. Kevin Ahern


  • Login