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Direct access to xenicane diterpenoids structure space and new insight in allenic transformations
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Wang, Huan. Direct access to xenicane diterpenoids structure space and new insight in allenic transformations. Retrieved from https://doi.org/doi:10.7282/T3KH0QNR

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TitleDirect access to xenicane diterpenoids structure space and new insight in allenic transformations
NameWang, Huan (author); Williams, Lawrence (chair); Seidel, Daniel (internal member); Knapp, Spencer (internal member); Lombardo, Louis (outside member); Rutgers University; Graduate School - New Brunswick
Date Created2016
Other Date2016-10 (degree)
SubjectChemistry and Chemical Biology, Allene
Extent1 online resource (ix, 379 p. : ill.)
DescriptionDisclosed in this dissertation are the design, synthesis, and preliminary biological evaluation of novel xeniolides that selectively activate apoptosis in precancerous cells. A divergent synthetic strategy to gain direct access to this semi-validated anticancer structure space from a single intermediate is designed. The chemical synthesis of this lynchpin compound, including a new Morita-Baylis-Hillman-type cyclization, new C-C fragmentation mechanistic insight, conversion of the lynchpin to a diverse set of related targets, and the identification, through biological evaluation, of new simplified, synthetic xeniolides that rival the parent natural products in terms of potency and especially in terms of selectivity. Catalytic allene osmylation featured by a five-step sequence to 4,10-didesmethyl (9S)-dihydro-erythronolide A and a mechanism study, and a molecular platform for catalytic allene epoxidation and a computational model explaining the stereochemical outcome are described.
NotePh.D.
NoteIncludes bibliographical references
Noteby Huan Wang
Genretheses, ETD doctoral
Persistent URLhttps://doi.org/doi:10.7282/T3KH0QNR
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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