The Total Synthesis of (-)-Detoxinine and (+)-Casuarine Using Tandem [4 + 2]/[3 + 2] Nitroalkene Cycloadditions and Cycloadditions of Nitroethylene
Hurd, Alexander Ross
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https://hdl.handle.net/2142/84466
Description
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
Issue Date
2000
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 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.
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