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Denmark, Scott E. Cottell, Jeromy John 2015-09-25T22:13:11Z 2015-09-25T22:13:11Z 10000-01-01 2004 2004 The successful synthesis of the (+)-scandine core began with a tandem conjugate addition/ [3+2] nitronate cycloaddition. This approach proceeded with high chemical yield and modest diastereoselectivity to provide an advanced bicyclic intermediate. Construction of two of the remaining three rings was accomplished by an intramolecular Heck cyclization of a pendant aryl iodide. This process proceeded with high diastereoselectivity to build vicinal quaternary centers. The final ring was created by reductive amination of a pyrrolidine aldehyde. This synthesis provided the core structure of (+/-)-scandine in 16 steps and 4.8% overall yield from 2,4-pentadienyl dimethyl malonate. Made available in DSpace on 2015-09-25T22:13:11Z (GMT). No. of bitstreams: 2 license.txt: 4848 bytes, checksum: 96035ab3f5e1c23cc7138a224ce498bd (MD5) 3153278.pdf: 21630243 bytes, checksum: bdc2dacc398f79c70017552b4a0b97e4 (MD5) Previous issue date: 2004 Embargo set by: Seth Robbins for item 85429 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 306 p. Thesis (Ph.D.)--University of Illinois at Urbana-Champaign, 2004. http://hdl.handle.net/2142/84148 (MiAaPQ)AAI3153278 eng Chemistry, Organic Tandem Cycloaddition Chemistry of Nitroalkenes: Total Synthesis of (+)-1-Epiaustraline and Synthesis of the Pentacyclic Core of (+/-)-Scandine text Chemistry Chemistry University of Illinois at Urbana-Champaign Dissertation Ph.D.