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Title:The Total Synthesis of (-)-Detoxinine and (+)-Casuarine Using Tandem [4 + 2]/[3 + 2] Nitroalkene Cycloadditions and Cycloadditions of Nitroethylene
Author(s):Hurd, Alexander Ross
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 first synthesis of (+)-casuarine, a pentahydroxy pyrrolizidine alkaloid of the alexine/australine subclass, is described. The key step is a tandem inter [4+2]/inter [3+2] nitroalkene cycloaddition involving an oxygenated nitroalkene, chiral vinyl ether, and vinyl silane dipolarophile, which establishes five of the six stereocenters present in this potent glycosidase inhibitor. The completion of the synthesis required only four additional steps to deliver the final product in 20% overall yield.
Issue Date:2000
Type:Text
Language:English
Description:217 p.
Thesis (Ph.D.)--University of Illinois at Urbana-Champaign, 2000.
URI:http://hdl.handle.net/2142/84466
Other Identifier(s):(MiAaPQ)AAI9955629
Date Available in IDEALS:2015-09-25
Date Deposited:2000


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