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Description
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 |
This item appears in the following Collection(s)
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Dissertations and Theses - Chemistry
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Graduate Dissertations and Theses at Illinois
Graduate Theses and Dissertations at Illinois