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Title:Efforts Toward the Total Synthesis of the Original and Revised Structures of Palau'amine
Author(s):Bultman, Michael Scott
Doctoral Committee Chair(s):Gin, David Y.
Department / Program:Chemistry
Degree Granting Institution:University of Illinois at Urbana-Champaign
Subject(s):Chemistry, Organic
Abstract: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.
Issue Date:2009
Description:315 p.
Thesis (Ph.D.)--University of Illinois at Urbana-Champaign, 2009.
Other Identifier(s):(UMI)AAI3406724
Date Available in IDEALS:2014-12-17
Date Deposited:2009

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