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dc.contributor.advisor Behar, Victor
dc.creatorSchaefer, Amber Rakowitz
dc.date.accessioned 2009-06-03T21:06:34Z
dc.date.available 2009-06-03T21:06:34Z
dc.date.issued 2007
dc.identifier.citation Schaefer, Amber Rakowitz. "Research toward the synthesis of heliquinomycin." (2007) Diss., Rice University. https://hdl.handle.net/1911/20647.
dc.identifier.urihttps://hdl.handle.net/1911/20647
dc.description.abstract Heliquinomycin, a member of a rubromycin family of natural products, is a complex natural product consisting of a naphthoquinone and an isocoumarin which are linked through a 5,6-spiroketal functionality. The spiroketal also bears a glycosidic linkage. Previous work in our group has developed a method for generating both the naphthoquinone and isocoumarin portions of this natural product. The focus of this work was to develop a method for joining these two halves of the natural product while also allowing for the formation of the spiroketal. The specific goals accomplished include developing a method for extending the allyl-side chain of a model isocoumarin compound, functionalization of an olefin in preparation for forming the spiroketal structure and coupling of the naphthoquinone with the isocoumarin model via a nitrile-oxide [3+2] dipolar cycloaddition. Completion of the natural product will also require several oxidation state adjustments of the naphthoquinone moiety. To that end we were able to carry out the necessary transformations: opening an isoxazole ring, reduction of a quinone ring to an acetylated hydroquinone and oxidation of a trimethoxybenzene ring to a methoxy quinone in attempting a synthesis of the natural product Y-1005.
dc.format.extent 172 p.
dc.format.mimetype application/pdf
dc.language.iso eng
dc.subjectOrganic chemistry
dc.title Research toward the synthesis of heliquinomycin
dc.type Thesis
dc.type.material Text
thesis.degree.department Chemistry
thesis.degree.discipline Natural Sciences
thesis.degree.grantor Rice University
thesis.degree.level Doctoral
thesis.degree.name Doctor of Philosophy


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