2026-09-22T20:57:45Z https://www.ideals.illinois.edu/oai-pmh

oai:www.ideals.illinois.edu:2142/84466 2023-07-11 col_2142_5131 col_2142_14789 com_2142_5130 com_2142_14788 com_2142_8903

Denmark, Scott E. Hurd, Alexander Ross 2015-09-25T22:14:38Z 2015-09-25T22:14:38Z 10000-01-01 2000 2000 The first synthesis of (+)-casuarine, a pentahydroxy pyrrolizidine alkaloid of the alexine/australine subclass, is described. The key step is a tandem inter [4+2]/inter [3+2] nitroalkene cycloaddition involving an oxygenated nitroalkene, chiral vinyl ether, and vinyl silane dipolarophile, which establishes five of the six stereocenters present in this potent glycosidase inhibitor. The completion of the synthesis required only four additional steps to deliver the final product in 20% overall yield. Made available in DSpace on 2015-09-25T22:14:38Z (GMT). No. of bitstreams: 2 license.txt: 4848 bytes, checksum: 96035ab3f5e1c23cc7138a224ce498bd (MD5) 9955629.pdf: 9425842 bytes, checksum: 1b4f47475db3b309e4ae7be0739df8d6 (MD5) Previous issue date: 2000 Embargo set by: Seth Robbins for item 85747 Lift date: Forever Reason: Restricted to the U of I community idenfinitely during batch ingest of legacy ETDs Restricted to the U of I community idenfinitely during batch ingest of legacy ETDs U of I Only 217 p. Thesis (Ph.D.)--University of Illinois at Urbana-Champaign, 2000. http://hdl.handle.net/2142/84466 (MiAaPQ)AAI9955629 eng Chemistry, Organic The Total Synthesis of (-)-Detoxinine and (+)-Casuarine Using Tandem [4 + 2]/[3 + 2] Nitroalkene Cycloadditions and Cycloadditions of Nitroethylene text Chemistry Chemistry University of Illinois at Urbana-Champaign Dissertation Ph.D.