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Description
Title: | The Asymmetric Total Synthesis of Cephalotaxine |
Author(s): | Eckelbarger, Joseph David |
Doctoral Committee Chair(s): | Gin, David Y. |
Department / Program: | Chemistry |
Discipline: | Chemistry |
Degree Granting Institution: | University of Illinois at Urbana-Champaign |
Degree: | Ph.D. |
Genre: | Dissertation |
Subject(s): | Chemistry, Organic |
Abstract: | A unique method for the formation of [3]benzazepines, via the [3,3]-sigmatropic rearrangement of 1-vinyl-2-aryl-aziridines, has been developed and applied to the synthesis of the Cephalotaxus alkaloids. The synthetic approach begins with D-ribose and utilizes the [3,3] sigmatropic rearrangement of a highly functionalized 1-vinyl-2-aryl aziridine and a diastereoselective intermolecular [3+2] cycloaddition of a non-stabilized azomethine ylide as the key steps. This work has resulted in an asymmetric total synthesis of cephalotaxine in 24 steps and 0.9% overall yield. |
Issue Date: | 2006 |
Type: | Text |
Language: | English |
Description: | 292 p. Thesis (Ph.D.)--University of Illinois at Urbana-Champaign, 2006. |
URI: | http://hdl.handle.net/2142/84220 |
Other Identifier(s): | (MiAaPQ)AAI3223583 |
Date Available in IDEALS: | 2015-09-25 |
Date Deposited: | 2006 |
This item appears in the following Collection(s)
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Dissertations and Theses - Chemistry
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Graduate Dissertations and Theses at Illinois
Graduate Theses and Dissertations at Illinois