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Spirodiepoxide-based cascade strategies to the upper hemisphere of pectenotoxin-4
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Xu, Da. Spirodiepoxide-based cascade strategies to the upper hemisphere of pectenotoxin-4. Retrieved from https://doi.org/doi:10.7282/T3HH6MQ2

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TitleSpirodiepoxide-based cascade strategies to the upper hemisphere of pectenotoxin-4
NameXu, Da (author); Williams, Lawrence J (chair); Daniel, Seidel (internal member); Roger, Jones A (internal member); Zhao, Hong (outside member); Rutgers University; Graduate School - New Brunswick
Date Created2014
Other Date2014-10 (degree)
SubjectChemistry and Chemical Biology, Ketones, Allene, Fragmentation reactions
Extent1 online resource (x, 393 p. : ill.)
DescriptionDisclosed are studies on allene oxidations and functionally diverse motif. The utilization of spirodiepoxide based methodologies in the synthesis of highly functionalized α-tetrahydrofuranyl-α'-hydroxy ketones led to a cascade strategy to the upper hemisphere of pectenotoxin-4. Remarkably, an advanced allene intermediate with six stereo centers and one epoxide was converted to a C1-C19 sector of pectenotoxin-4 with 9 stereo centers including 3 rings in one pot and 26% yield. It is also shown that electrophile capture with osmium enolates resulted in anti-α-halo-α’-hydroxyketone products. This method complements our spirodiepoxide chemistry in stereroselective conversion of chiral allenes. Finally, we envisioned that a cyclodecatrienone, prepared via C-C fragmentation of a cis-decalin derivative, could be built up to Vernonia allenes and other structurally related germacranes by taking advantage of our allene chemistry.
NotePh.D.
NoteIncludes bibliographical references
Noteby Da Xu
Genretheses, ETD doctoral
Persistent URLhttps://doi.org/doi:10.7282/T3HH6MQ2
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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