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Gin, David Y. Eckelbarger, Joseph David 2015-09-25T22:13:32Z 2015-09-25T22:13:32Z 10000-01-01 2006 2006 A unique method for the formation of [3]benzazepines, via the [3,3]-sigmatropic rearrangement of 1-vinyl-2-aryl-aziridines, has been developed and applied to the synthesis of the Cephalotaxus alkaloids. The synthetic approach begins with D-ribose and utilizes the [3,3] sigmatropic rearrangement of a highly functionalized 1-vinyl-2-aryl aziridine and a diastereoselective intermolecular [3+2] cycloaddition of a non-stabilized azomethine ylide as the key steps. This work has resulted in an asymmetric total synthesis of cephalotaxine in 24 steps and 0.9% overall yield. Made available in DSpace on 2015-09-25T22:13:32Z (GMT). No. of bitstreams: 2 license.txt: 4848 bytes, checksum: 96035ab3f5e1c23cc7138a224ce498bd (MD5) 3223583.pdf: 6003327 bytes, checksum: 0876cce6570adc0667d54965ae2e4afd (MD5) Previous issue date: 2006 Embargo set by: Seth Robbins for item 85501 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 292 p. Thesis (Ph.D.)--University of Illinois at Urbana-Champaign, 2006. http://hdl.handle.net/2142/84220 (MiAaPQ)AAI3223583 eng Chemistry, Organic The Asymmetric Total Synthesis of Cephalotaxine text Chemistry Chemistry University of Illinois at Urbana-Champaign Dissertation Ph.D.