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STUDIES TOWARDS THE TOTAL SYNTHESIS OF VANCOMYCIN AGLYCON

Basu, Shubhamita
http://rave.ohiolink.edu/etdc/view?acc_num=case1183157258

Abstract Details

2007, Doctor of Philosophy, Case Western Reserve University, Chemistry.
Vancomycin is a glycopeptide antibiotic, clinically the last resort for physicians to combat deadly bacterial infection. The complex structural motif along with the numerous stereocenters has made it a challenging target for synthetic chemists. Emerging bacterial resistance against vancomycin has inspired scientists to look at its synthesis from the standpoint of developing new antibiotics. In this work, application of the ruthenium-mediated SNAr reaction was explored to synthesize the aryl ether linkage, that is a key structural feature of vancomycin. Two different pathways were investigated for this purpose (Chapter 2 and Chapter 3), and while the pathways were not greatly successful, they helped us understand the different facets of reactivity of the ruthenium complexes. In Chapter 3, the ruthenium-promoted SNAr reaction was tested on molecules with two different halides that can be displaced, and the chemoselectivity of such displacement was examined. While fluoride is displaced selectively over chloride in the case of amine nucleophiles, the opposite happened when the reaction was done with phenoxides. This prompted us to revisit the standard mechanistic dogma of metal-promoted SNAr reactions and rationalize the experimental results in light of both electronegativity and leaving group ability.
Anthony Pearson (Advisor)
Chemistry, Organic
vancomycin; glycopeptide antibiotics; ruthenium-mediated SNAr

Recommended Citations

Citations

  • Basu, S. (2007). STUDIES TOWARDS THE TOTAL SYNTHESIS OF VANCOMYCIN AGLYCON [Doctoral dissertation, Case Western Reserve University]. OhioLINK Electronic Theses and Dissertations Center. http://rave.ohiolink.edu/etdc/view?acc_num=case1183157258

    APA Style (7th edition)

  • Basu, Shubhamita. STUDIES TOWARDS THE TOTAL SYNTHESIS OF VANCOMYCIN AGLYCON. 2007. Case Western Reserve University, Doctoral dissertation. OhioLINK Electronic Theses and Dissertations Center, http://rave.ohiolink.edu/etdc/view?acc_num=case1183157258.

    MLA Style (8th edition)

  • Basu, Shubhamita. "STUDIES TOWARDS THE TOTAL SYNTHESIS OF VANCOMYCIN AGLYCON." Doctoral dissertation, Case Western Reserve University, 2007. http://rave.ohiolink.edu/etdc/view?acc_num=case1183157258

    Chicago Manual of Style (17th edition)

case1183157258
2,958
© 2007, all rights reserved.
This open access ETD is published by Case Western Reserve University School of Graduate Studies and OhioLINK.