Studies directed toward the synthesis of the A-ring of taxol.
Item
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Title
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Studies directed toward the synthesis of the A-ring of taxol.
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Identifier
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AAI9304673
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identifier
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9304673
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Creator
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Hamilton, Pauline McDonald.
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Contributor
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W. F. Berkowitz
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Date
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1992
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Language
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English
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Publisher
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City University of New York.
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Subject
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Chemistry, Organic | Health Sciences, Oncology | Chemistry, Pharmaceutical
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Abstract
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Taxol 1, a novel anticancer agent, isolated from Taxus brevifolia, is a member of the class of taxane diterpenes. Since its isolation and characterization (in 1971 by Wall and collaborators) many groups around the world using varied approaches have made significant contributions toward the assembly of the taxane framework and ultimately to taxol itself.;The focus of this investigation was directed towards making a fully functionalized A-ring synthon of taxol. Toward this end three approaches were explored. These approaches to the A-ring involve a Robinson annulation, an alkoxide accelerated vinylcyclobutane to cyclohexenol rearrangement (developed by Danheiser), and acid catalyzed electrophilic cyclization of geranyl acetate and its derivatives. Early difficulties with the alkoxide accelerated ring expansion approach resulted in it being aborted. The other two approaches led to interesting intermediates with the requisite number of carbon atoms and latent functionalities. However, later efforts to transform these intermediates to the targeted A-ring synthon (93), were futile.(DIAGRAM, TABLE OR GRAPHIC OMITTED...PLEASE SEE DAI).
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Type
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dissertation
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Source
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PQT Legacy CUNY.xlsx
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degree
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Ph.D.
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Program
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Chemistry
