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oai:www.ideals.illinois.edu:2142/18298 2023-07-10 col_2142_5131 col_2142_14789 com_2142_5130 com_2142_14788 com_2142_8903

Gin, David Y. Gin, David Y. Hergenrother, Paul J. Burke, Martin D. McCall, Benjamin J. Wilmot, Jeremy T. 2011-01-14T22:45:20Z 2011-01-14T22:45:20Z 2011-01-14T22:45:20Z The Cephalotaxus esters are a class of alkaloids extracted from plants of the Cephalotaxus genus and have been shown to be potent inhibitors of P-388 murine leukemia cells. While direct acylation of cephalotaxine has been reported to be difficult, the construction and acylation of cephalotaxine using a β-lactone acyl chain surrogate in the synthesis of anhydroharringtonine, deoxyharringtonine, homodeoxyharringtonine, and homoharringtonine is described. The natural esters as well as several non-natural analogues were tested against various human cancer cell lines not previously challenged by these alkaloids. Variations in the structure of the ester chain were found to confer differing activity profiles against vincristine resistant HL-60/RV+. The Aconitum and Delphinium alkaloids comprise a family of compounds isolated from the Aconitum and Delphinium genera. Several compounds within this class show potent Na+ ion channel activity ranging from the ion channel activation of aconitine to the ion channel blocking of lappaconitine. The completed synthesis of the skeleton of the C19-diterpenoid alkaloids is described. Key steps include a Diels–Alder cycloaddition of a cyclopropene with a 2,5-dioxycyclopenta-1,3-diene, a second Diels–Alder cycloaddition with a 2,5-dihydroazepine 2π component, an intramolecular N-acyliminium cyclization, and a radical conjugate addition. Item withdrawn by Mark Zulauf (zulauf@illinois.edu) on 2010-12-01T14:25:57Z Item was in collections: University of Illinois Theses & Dissertations (ID: 1) No. of bitstreams: 1 Wilmot_Jeremy.pdf: 2044707 bytes, checksum: e588cb6aa3198c882f7bf99429687c69 (MD5) Made available in DSpace on 2011-01-14T22:45:20Z (GMT). No. of bitstreams: 2 Wilmot_Jeremy.pdf: 3051188 bytes, checksum: 4f780e55c4fd3612d2c6fc96842dc74d (MD5) license.txt: 4067 bytes, checksum: 0664ff62e1b16630b740934fd73ed4a7 (MD5) http://hdl.handle.net/2142/18298 en Copyright 2010 Jeremy Todd Wilmot 2010-12 cephalotaxine cephalotaxus esters harringtonine homoharringtonine homodeoxyharringtonine anhydroharringtonine deoxyharringtonine total synthesis natural products aconitum delphinium C19-diterpenoids aconitine alkaloid radical N-acyl iminium iminium radical conjugate addition ion channel deoxyhomoharringtonine Complex botanical natural products: Synthesis of cephalotaxus esters and of the C19-diterpenoid skeleton of aconitum and delphinium alkaloids Chemistry 1413 Chemistry 0335 University of Illinois at Urbana-Champaign Dissertation Ph.D. PHD:Chemistry -UIUC 10KS0335PHD