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Carbenoid Insertion Chemistry on Furanose Platforms as a Route to Natural Product Frameworks

Patton, Jennie L.
http://rave.ohiolink.edu/etdc/view?acc_num=ysu1219534151

Abstract Details

2008, Master of Science in Chemistry, Youngstown State University, Department of Chemistry.
The following describes a successful synthetic pathway to create an analog of the natural product (+)-dihydrocanadensolide from the inexpensive and readily available D-xylose. The pathway will describe protecting group chemistry, an esterification, a diazo transfer reaction, and the key step being a metal-catalyzed intramolecular insertion reaction. The metal catalyst used in this step is rhodium(II) acetate and it will be shown to catalyze the decomposition of a diazoester, thus creating a new carbon-carbon bond by carbenoid insertion chemistry. The end result is a bicyclic compound with a fused furan ring system common to many important and useful natural products.
Peter Norris, PhD (Advisor)
John Jackson, PhD (Committee Member)
Michael Serra, PhD (Committee Member)
160 p.
Biomedical Research; Chemistry; Experiments; Organic Chemistry; Pharmaceuticals
carbohydrate; natural products; lactone; rhodium(II) acetate; carbenoid; xylose; diazo

Recommended Citations

Citations

  • Patton, J. L. (2008). Carbenoid Insertion Chemistry on Furanose Platforms as a Route to Natural Product Frameworks [Master's thesis, Youngstown State University]. OhioLINK Electronic Theses and Dissertations Center. http://rave.ohiolink.edu/etdc/view?acc_num=ysu1219534151

    APA Style (7th edition)

  • Patton, Jennie. Carbenoid Insertion Chemistry on Furanose Platforms as a Route to Natural Product Frameworks. 2008. Youngstown State University, Master's thesis. OhioLINK Electronic Theses and Dissertations Center, http://rave.ohiolink.edu/etdc/view?acc_num=ysu1219534151.

    MLA Style (8th edition)

  • Patton, Jennie. "Carbenoid Insertion Chemistry on Furanose Platforms as a Route to Natural Product Frameworks." Master's thesis, Youngstown State University, 2008. http://rave.ohiolink.edu/etdc/view?acc_num=ysu1219534151

    Chicago Manual of Style (17th edition)

ysu1219534151
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© 2008, all rights reserved.
This open access ETD is published by Youngstown State University and OhioLINK.