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oai:www.ideals.illinois.edu:2142/72262 2023-07-11 col_2142_5131 col_2142_14789 com_2142_5130 com_2142_14788 com_2142_8903

Gin, David Y. Bultman, Michael Scott 2014-12-17T21:28:56Z 2014-12-17T21:28:56Z 10000-01-01 2009 2009 Our developments toward the total synthesis of the original and revised structures of palau'amine are presented in this study. This includes the construction of the fully functionalized cyclopentane cores of both the original and revised structures via the application of a Diels-Alder/[3,3]-sigmatropic rearrangement of tricyclodecadienes. A cyclization strategy for the formation of the strained trans-fused azabicyclo[3.3.0]octane bicyclic system of the core of the revised structure of palau'amine was also developed within the context the natural product analogs dimethylcyclopentaphakellin and 10,6-epidimethylcyclopentaphakellin utilizing an intramolecular azide [3+2]-dipolar cycloaddition. Also of note is the development of new methods for the preparation of the polycyclic pyrazinones. Application of this cyclization strategy has allowed for synthesis of the advanced intermediates possessing the fully functionalized skeleton of the revised structure of palau'amine encompassing the A, E, and D rings. Made available in DSpace on 2014-12-17T21:28:56Z (GMT). No. of bitstreams: 1 3406724.pdf: 12699019 bytes, checksum: d283711a87b0c8329c61933d9bf97a01 (MD5) Previous issue date: 2009 Embargo set by: Seth Robbins for item 72430 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 315 p. Thesis (Ph.D.)--University of Illinois at Urbana-Champaign, 2009. http://hdl.handle.net/2142/72262 (UMI)AAI3406724 Chemistry, Organic Efforts Toward the Total Synthesis of the Original and Revised Structures of Palau'amine text Chemistry Chemistry University of Illinois at Urbana-Champaign Dissertation Ph.D.