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Studies Towards the Total Synthesis of Ristocetin A and Orienticin C Aglycones

Ciurea, Diana Victoria
http://rave.ohiolink.edu/etdc/view?acc_num=case1192565744

Abstract Details

2008, Doctor of Philosophy, Case Western Reserve University, Chemistry.
Vancomycin-related glycopeptides constitute a large family of clinically important antibiotics, used as drugs of last resort in treating infections caused by methicillin-resistant Staphylococcus aureus. However, the frequency of vancomycin resistant pathogens has increased significantly over the past decade, prompting an interest in the development of synthetic and semi-synthetic glycopeptides. The research work presented in this thesis has been focused on the application of ruthenium-mediated SNAr methodology for the synthesis of diaryl ether linkages both inter- and intramolecularly. As described in chapter two, our efforts first targeted the synthesis of the F-O-G subunit 2.8 of ristocetin A via an intermolecular SNAr reaction between the phenolic OH of the Teoc protected F amino alcohol 2.9 and the chloro substituent of the amino alcohol corresponding to G ring 2.10. Considerable competing demetalation of the starting material G-ruthenium complex 2.10 occurred during the attempted coupling, which was overcome by stepwise addition of the solid G-ruthenium complex 2.10 to the reaction mixture increasing the yield of this transformation to 66% yield. Chapter three provides details for the construction of the intermediate 3.3, a tripeptido-arene-ruthenium complex, required for a projected synthesis of orienticin C aglycone 3.1. Also, a model study on ruthenium-mediated macrocyclization for the formation of the 16-membered diaryl ether ring 3.32 was investigated, assuring the applicability of this approach to the synthesis of orienticin C aglycone.
Anthony Pearson (Advisor)
Chemistry, Organic
Vancomycin; equiv; 1H; RISTOCETIN; Diaryl; OMe

Recommended Citations

Citations

  • Ciurea, D. V. (2008). Studies Towards the Total Synthesis of Ristocetin A and Orienticin C Aglycones [Doctoral dissertation, Case Western Reserve University]. OhioLINK Electronic Theses and Dissertations Center. http://rave.ohiolink.edu/etdc/view?acc_num=case1192565744

    APA Style (7th edition)

  • Ciurea, Diana. Studies Towards the Total Synthesis of Ristocetin A and Orienticin C Aglycones. 2008. Case Western Reserve University, Doctoral dissertation. OhioLINK Electronic Theses and Dissertations Center, http://rave.ohiolink.edu/etdc/view?acc_num=case1192565744.

    MLA Style (8th edition)

  • Ciurea, Diana. "Studies Towards the Total Synthesis of Ristocetin A and Orienticin C Aglycones." Doctoral dissertation, Case Western Reserve University, 2008. http://rave.ohiolink.edu/etdc/view?acc_num=case1192565744

    Chicago Manual of Style (17th edition)

case1192565744
2,117
© 2007, all rights reserved.
This open access ETD is published by Case Western Reserve University School of Graduate Studies and OhioLINK.