Penicillin V research

Penicillin V

Your outline should address:

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The discovery of your molecule (who, when, where)

Structural features of interest (chiral centers, functional groups, rings, conjugated pi bonds, etc.) in your molecule

Steps of interest from one or more published syntheses of your molecule

The utility or research interest of your molecule

  • Your outline must include a peer-reviewed resource that you will use in writing your paper. An example of this outline has been provided for you in the submodules below.
  • Here are also some great places to find sources:
  • Google Scholar
  • ACS Journal of Organic Chemistry (and others!)
  • PubMed

    I will add a sample of how it should be.

    Paclitaxel (Taxol)
    {Disclaimer: You are not required to include an image of your molecule. This example is also intentionally
    Discovery: (Cragg)

    Structure and isolation paclitaxel, trade name Taxol, was first published in 1971

    Source: Organic extract of Taxus brevifolia (Pacific Yew) bark

    Bark extract was found to have KB cytotoxicity in 1962- screening program of the Cancer
    Chemotherapy National Service Center (CCNSC)

    Paclitaxel was found to exhibit in vivo anti-cancer activity against many model cell lines
    Structure: (Silverman and Holladay)

    Fused tetracyclic carbon skeleton composed of a cyclohexene, a cyclooctenone (cyclooctane
    with a ketone), a cyclohexane and a fused chiral oxetane (4-atom cyclic ether)

    Functional Groups: 1 amide, 3 alcohols, 1 ketone, 1 fused oxetane, 4 esters, 1 E-cycloalkene

    Conjugated systems: 3 phenyl rings

    Stereocenters: 11 total, including amongst others the amide (S), every ester and alcohol, methyl
    group (R), and the fused oxetane (R, S)
    Synthesis: (Nicolaou and Sorensen)

    1994 K. C. Nicolaou synthesis is 37 steps long to synthesize (-)-taxol

    Diels-Alder reaction: creates the cyclohexene ring

    Shapiro coupling: creates a bond between chiral tertiary alcohol and chiral benzoyl (phenyl ester)
    in the cyclooctanone

    McMurry coupling: creates a bond between a chiral acetyl (methyl ester) and the ketone of the

    PCC is used to make the single ketone in a regiospecific fashion
    Utility/ Interest: (Weaver)

    Long considered a “white whale” of natural product synthesis (uncited)

    Name “taxol” comes from Taxus tree source and the presence of multiple hydroxyl groups

    Used to treat several cancers, including head, neck, prostate, and cervical cancers

    Some studies suggest that the mechanism of taxol’s cytotoxic effects is mitotic arrest through
    promoting microtubule stabilization

    Recent studies suggest that taxol’s mechanism of action is chromosome missegregation
    References Cited:
    1. Cragg, Gordon M. “Paclitaxel (Taxol®): A Success Story With Valuable Lessons for Natural Product
    Drug Discovery and Development.” Medicinal Research Reviews, vol. 18, no. 5, Wiley, Aug. 1998,
    pp. 315–31.
    2. Nicolaou, K., and E. Sorensen. Classics in Total Synthesis: Targets, Strategies, Methods. Hoboken, NJ,
    United States, Wiley, 1996.
    3. Silverman Richard Ph. D. Organic, and Mark Holladay. The Organic Chemistry of Drug Design and Drug
    Action. 3rd ed., Academic Press, 2014.
    4. Weaver, Beth A. “How Taxol/Paclitaxel Kills Cancer Cells.” Molecular Biology of the Cell, edited by
    William Bement, vol. 25, no. 18, American Society for Cell Biology (ASCB), Sept. 2014, pp. 2677–

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