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Title:Tandem Double Intramolecular [4+2]/[3+2] Cycloaddition of Nitro Olefins: Part I: Construction of Piperidine Rings. Part II: Construction of Vicinal Quaternary Stereogenic Centers. Part III: Progress Toward a Total Synthesis of Daphnilactone B
Author(s):Baiazitov, Ramil Yashnurovich
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 fully functionalized nitroalkene intermediate for the total synthesis of daphnilactone has also been prepared and participated in the high yielding tandem double-intramolecular [4+2]/[3+2] cycloaddition to provide a mixture of two epimeric nitroso acetals. Ozonolysis of the cycloadducts, followed by hydrogenolysis and intramolecular acylation provided the intermediates for the total synthesis that may be elaborated to daphnilactone B. Possible routes to complete the synthesis are also discussed.
Issue Date:2007
Type:Text
Language:English
Description:385 p.
Thesis (Ph.D.)--University of Illinois at Urbana-Champaign, 2007.
URI:http://hdl.handle.net/2142/84254
Other Identifier(s):(MiAaPQ)AAI3269837
Date Available in IDEALS:2015-09-25
Date Deposited:2007


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