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Efforts Toward the Total Synthesis of the Original and Revised Structures of Palau'amine
Bultman, Michael Scott
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https://hdl.handle.net/2142/14694
Description
- Title
- Efforts Toward the Total Synthesis of the Original and Revised Structures of Palau'amine
- Author(s)
- Bultman, Michael Scott
- Issue Date
- 2010-01-06T16:39:36Z
- Director of Research (if dissertation) or Advisor (if thesis)
- Gin, David Y.
- Doctoral Committee Chair(s)
- Gin, David Y.
- Committee Member(s)
- Denmark, Scott E.
- Katzenellenbogen, John A.
- Girolami, Gregory S.
- Department of Study
- Chemistry
- Discipline
- Chemistry
- Degree Granting Institution
- University of Illinois at Urbana-Champaign
- Degree Name
- Ph.D.
- Degree Level
- Dissertation
- Date of Ingest
- 2010-01-06T16:39:36Z
- Keyword(s)
- palau'amine
- alkaloid
- natural product
- synthetic studies
- 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 cylcoaddition. 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.
- Graduation Semester
- 2009-12
- Permalink
- http://hdl.handle.net/2142/14694
- Copyright and License Information
- © Copyright by Michael Scott Bultman, 2009
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Graduate Dissertations and Theses at Illinois PRIMARY
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