Tandem Cycloaddition Chemistry of Nitroalkenes: Total Synthesis of (+)-1-Epiaustraline and Synthesis of the Pentacyclic Core of (+/-)-Scandine
Cottell, Jeromy John
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https://hdl.handle.net/2142/84148
Description
Title
Tandem Cycloaddition Chemistry of Nitroalkenes: Total Synthesis of (+)-1-Epiaustraline and Synthesis of the Pentacyclic Core of (+/-)-Scandine
Author(s)
Cottell, Jeromy John
Issue Date
2004
Doctoral Committee Chair(s)
Denmark, Scott E.
Department of Study
Chemistry
Discipline
Chemistry
Degree Granting Institution
University of Illinois at Urbana-Champaign
Degree Name
Ph.D.
Degree Level
Dissertation
Keyword(s)
Chemistry, Organic
Language
eng
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.
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