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oai:www.ideals.illinois.edu:2142/84254 2023-07-11 col_2142_5131 col_2142_14789 com_2142_5130 com_2142_14788 com_2142_8903

Denmark, Scott E. Baiazitov, Ramil Yashnurovich 2015-09-25T22:13:40Z 2015-09-25T22:13:40Z 10000-01-01 2007 2007 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. Made available in DSpace on 2015-09-25T22:13:40Z (GMT). No. of bitstreams: 2 license.txt: 4848 bytes, checksum: 96035ab3f5e1c23cc7138a224ce498bd (MD5) 3269837.pdf: 9130903 bytes, checksum: 1777486760365e6ee6e52b3ffba79579 (MD5) Previous issue date: 2007 Embargo set by: Seth Robbins for item 85535 Lift date: Forever Reason: Restricted to the U of I community idenfinitely during batch ingest of legacy ETDs Restricted to the U of I community idenfinitely during batch ingest of legacy ETDs U of I Only 385 p. Thesis (Ph.D.)--University of Illinois at Urbana-Champaign, 2007. http://hdl.handle.net/2142/84254 (MiAaPQ)AAI3269837 eng Chemistry, Organic 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 text Chemistry Chemistry University of Illinois at Urbana-Champaign Dissertation Ph.D.