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Title:Asymmetric Total Synthesis of (+)-Nominine: Development of a Dual Cycloaddition Strategy for the Synthesis of the Hetisine Alkaloids
Author(s):Peese, Kevin M.
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 dual cycloaddition strategy for the synthesis of the hetisine alkaloids has been developed and applied to the asymmetric total synthesis of nominine. The approach relies on an early stage intramolecular aza-1,3-dipolar cycloaddition of a 4-oxidoisoquinolinium betaine with an ene-nitrile dipolarophile and a late stage intramolecular [4+2] Diels-Alder cycloaddition. Also of note is the development of a new method for the preparation of 4-oxidoisoquinolinium betaines. Overall, a 16 step asymmetric synthesis of (+)-nominine was accomplished in 1.3% yield, while (+/-)-nominine was prepared in 15 steps in 6.1% yield.
Issue Date:2007
Type:Text
Language:English
Description:313 p.
Thesis (Ph.D.)--University of Illinois at Urbana-Champaign, 2007.
URI:http://hdl.handle.net/2142/84279
Other Identifier(s):(MiAaPQ)AAI3290348
Date Available in IDEALS:2015-09-25
Date Deposited:2007


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