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Allene cycloisomerization, epoxidation, and applications in total synthesis
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Cusick, Joseph Ryan. Allene cycloisomerization, epoxidation, and applications in total synthesis. Retrieved from https://doi.org/doi:10.7282/T3P26X7K

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TitleAllene cycloisomerization, epoxidation, and applications in total synthesis
NameCusick, Joseph Ryan (author); Williams, Lawrence J (chair); Knapp, Spencer (internal member); Hultzsch, Kai (internal member); Supplee, Carolyn (outside member); Rutgers University; Graduate School - New Brunswick
Date Created2011
Other Date2011-10 (degree)
SubjectChemistry and Chemical Biology, Allene—Synthesis
Extentxix, 398 p. : ill.
DescriptionDisclosed are studies on the structure and reactivity of allenes and spirodiepoxides (SDEs) and their application to synthesis. A novel ruthenium promoted cycloisomerization of γ-enallenes to cyclopentenes was discovered. The effects of solvent, oxidant, and substrate structure on the stereoselectivity of SDE formation from 1,3-disubstituted and trisubstituted allenes were evaluated. A computational model was advanced for the rationalization of observed selectivity in such formations. The known acid instability of SDEs was exploited to effect a designed rearrangement of β-silyl SDE to an α-hydroxy enone. Silyl-substituted SDEs were utilized to give carbinol substituted heterocycles with excellent ee, α-hydroxy enones, as well as α,β-dihydroxy olefins. A silyl-SDE approach was used to accomplish a short and efficient total synthesis of the natural product, epi-citreodiol. A de novo synthesis of the anticancer natural product jaspine B was also achieved using a SDE-based approach.
NotePh.D.
NoteIncludes bibliographical references
NoteIncludes vita
Noteby Joseph Ryan Cusick
Genretheses, ETD doctoral
Persistent URLhttps://doi.org/doi:10.7282/T3P26X7K
Languageeng
CollectionGraduate School - New Brunswick Electronic Theses and Dissertations
Organization NameRutgers, The State University of New Jersey
RightsThe author owns the copyright to this work.
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