I. "One-pot" cyclopentenone synthesis via the acetonyl synthetic equivalent 3-chloro-2-diethylphosphoryloxy-1-propene ; II. Isolation and characterization of cycloseychellene from patchouli oil

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dc.contributor.advisorWelch, Steven C.
dc.contributor.committeeMemberDyckes, Douglas F.
dc.contributor.committeeMemberKohn, Harold Lewis
dc.contributor.committeeMemberKadish, Karl M.
dc.contributor.committeeMemberLemke, Thomas L.
dc.creatorAssercq, Jean-Marie
dc.date.accessioned2024-01-24T17:20:29Z
dc.date.available2024-01-24T17:20:29Z
dc.date.issued1985
dc.description.abstractA new acetonyl synthetic equivalent 3-chloro-2-diethyl- phosphoryloxy-l-propene is reported. This reagent can undergo alkylation, then hydrolysis under mild acidic conditions to afford an acetonyl unit. More interestingly, utilization of this reagent permits a convenient "one-pot" conversion of a ketone to a cyclopentenone. Short syntheses of various cyclopentenones via this route, alkylation of an enolate anion with 3-chloro-2-diethyl- phosphoryloxy-l-propene followed by in situ base hydrolysis, is described. Applications of this methodology to new syntheses of cis-jasmone, and methylenomycin B are also described. The isolation of the sesquiterpene cycloseychellene from West Indian Patchouli Oil is described.
dc.description.departmentChemistry, Department of
dc.format.digitalOriginreformatted digital
dc.format.mimetypeapplication/pdf
dc.identifier.other13034206
dc.identifier.urihttps://hdl.handle.net/10657/16058
dc.language.isoen
dc.rightsThis item is protected by copyright but is made available here under a claim of fair use (17 U.S.C. Section 107) for non-profit research and educational purposes. Users of this work assume the responsibility for determining copyright status prior to reusing, publishing, or reproducing this item for purposes other than what is allowed by fair use or other copyright exemptions. Any reuse of this item in excess of fair use or other copyright exemptions requires express permission of the copyright holder.
dc.subjectCyclopentenone
dc.subjectCycloseychellene
dc.titleI. "One-pot" cyclopentenone synthesis via the acetonyl synthetic equivalent 3-chloro-2-diethylphosphoryloxy-1-propene ; II. Isolation and characterization of cycloseychellene from patchouli oil
dc.type.dcmiText
dc.type.genreThesis
thesis.degree.collegeCollege of Natural Sciences and Mathematics
thesis.degree.departmentChemistry, Department of
thesis.degree.disciplineChemistry
thesis.degree.grantorUniversity of Houston
thesis.degree.levelDoctoral
thesis.degree.nameDoctor of Philosophy

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