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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


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