Penicillin V research

Penicillin V

Your outline should address:

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

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
complex.}
Discovery: (Cragg)
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Structure and isolation paclitaxel, trade name Taxol, was first published in 1971
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Source: Organic extract of Taxus brevifolia (Pacific Yew) bark
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Bark extract was found to have KB cytotoxicity in 1962- screening program of the Cancer
Chemotherapy National Service Center (CCNSC)
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Paclitaxel was found to exhibit in vivo anti-cancer activity against many model cell lines
Structure: (Silverman and Holladay)
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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)
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Functional Groups: 1 amide, 3 alcohols, 1 ketone, 1 fused oxetane, 4 esters, 1 E-cycloalkene
(isolated)
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Conjugated systems: 3 phenyl rings
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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)
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1994 K. C. Nicolaou synthesis is 37 steps long to synthesize (-)-taxol
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Diels-Alder reaction: creates the cyclohexene ring
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Shapiro coupling: creates a bond between chiral tertiary alcohol and chiral benzoyl (phenyl ester)
in the cyclooctanone
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McMurry coupling: creates a bond between a chiral acetyl (methyl ester) and the ketone of the
cyclooctanone
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PCC is used to make the single ketone in a regiospecific fashion
Utility/ Interest: (Weaver)
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Long considered a “white whale” of natural product synthesis (uncited)
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Name “taxol” comes from Taxus tree source and the presence of multiple hydroxyl groups
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Used to treat several cancers, including head, neck, prostate, and cervical cancers
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Some studies suggest that the mechanism of taxol’s cytotoxic effects is mitotic arrest through
promoting microtubule stabilization
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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. https://doi.org/10.1002/(sici)1098-1128(199809)18:5.
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–
81. https://doi.org/10.1091/mbc.e14-04-0916.