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Title:Tandem Cycloaddition Chemistry of Nitroalkenes: Total Synthesis of (+)-1-Epiaustraline and Synthesis of the Pentacyclic Core of (+/-)-Scandine
Author(s):Cottell, Jeromy John
Doctoral Committee Chair(s):Denmark, Scott E.
Department / Program:Chemistry
Discipline:Chemistry
Degree Granting Institution:University of Illinois at Urbana-Champaign
Degree:Ph.D.
Genre:Dissertation
Subject(s):Chemistry, Organic
Abstract:The successful synthesis of the (+)-scandine core began with a tandem conjugate addition/ [3+2] nitronate cycloaddition. This approach proceeded with high chemical yield and modest diastereoselectivity to provide an advanced bicyclic intermediate. Construction of two of the remaining three rings was accomplished by an intramolecular Heck cyclization of a pendant aryl iodide. This process proceeded with high diastereoselectivity to build vicinal quaternary centers. The final ring was created by reductive amination of a pyrrolidine aldehyde. This synthesis provided the core structure of (+/-)-scandine in 16 steps and 4.8% overall yield from 2,4-pentadienyl dimethyl malonate.
Issue Date:2004
Type:Text
Language:English
Description:306 p.
Thesis (Ph.D.)--University of Illinois at Urbana-Champaign, 2004.
URI:http://hdl.handle.net/2142/84148
Other Identifier(s):(MiAaPQ)AAI3153278
Date Available in IDEALS:2015-09-25
Date Deposited:2004


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