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Approaches to the Synthesis of the Natural Products, Azaphorbol and Frondosin B, via Diazo Decomposition Reactions

Frantz, Alicia J.
http://rave.ohiolink.edu/etdc/view?acc_num=ohiou1478781611670221

Abstract Details

2016, Doctor of Philosophy (PhD), Ohio University, Chemistry and Biochemistry (Arts and Sciences).
The use of carbonyl ylides as reactive intermediates has numerous potential applications in the field of natural product synthesis. These highly reactive intermediates can be formed from the metal catalyzed diazo-decomposition reactions. They can undergo several subsequent reactions, including the 1,3-dipolar cycloaddition reaction, resulting in bridged oxygen heterocycles. Use of 1,3-dipolar cycloaddition reactions can be used to generate the seven and six membered rings of the bicycle[5.4.0]undecene core of various natural products. The natural product phorbol belongs to the tigliane diterpene family and is a protein kinase C (PKC) activator. Of the compounds belonging to the phorbol family, many show biological activity (e.g., tumor promotion, HIV inhibition, and antileukemic activity). Nitrogen containing derivatives of phorbol (azaphorbol) are relatively rare in the literature. An efficient route to the azaphorbol core will enable the generation of analogs to be investigated for biological activity. Another natural product containing the bicycle[5.4.0]core is frondosin B. Frondosin B also shows biological activity by the inhibition of interleukin-8 (IL-8) and PKC inhibition. Generation of the core of these natural products is attempted via the rhodium(II) catalyzed 1,3-dipolar cycloaddition reaction. We have also devised a synthetic route to the unsubstituted cyclic diazoacetamides, a precursor to the 1,3-dipolar cycloaddition reaction, successfully. These diazo-moieties can play a role in late stage synthesis and the discovery of a facile, high yielding route is highly valuable.
Mark McMills (Advisor)
153 p.
Chemistry; Organic Chemistry
azaphorbol; phorbol; frondosin B; 1,3-diploar cycloaddition; diazoacetamide; rhodium II; diazo decomposition reaction

Recommended Citations

Citations

  • Frantz, A. J. (2016). Approaches to the Synthesis of the Natural Products, Azaphorbol and Frondosin B, via Diazo Decomposition Reactions [Doctoral dissertation, Ohio University]. OhioLINK Electronic Theses and Dissertations Center. http://rave.ohiolink.edu/etdc/view?acc_num=ohiou1478781611670221

    APA Style (7th edition)

  • Frantz, Alicia. Approaches to the Synthesis of the Natural Products, Azaphorbol and Frondosin B, via Diazo Decomposition Reactions. 2016. Ohio University, Doctoral dissertation. OhioLINK Electronic Theses and Dissertations Center, http://rave.ohiolink.edu/etdc/view?acc_num=ohiou1478781611670221.

    MLA Style (8th edition)

  • Frantz, Alicia. "Approaches to the Synthesis of the Natural Products, Azaphorbol and Frondosin B, via Diazo Decomposition Reactions." Doctoral dissertation, Ohio University, 2016. http://rave.ohiolink.edu/etdc/view?acc_num=ohiou1478781611670221

    Chicago Manual of Style (17th edition)

ohiou1478781611670221
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This open access ETD is published by Ohio University and OhioLINK.