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 Copy

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

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

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http://hdl.handle.net/2142/14694

Copyright and License Information

© Copyright by Michael Scott Bultman, 2009

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