Development of Organocatalyzed Enantioselective Conjugate Addition and Application to the Total Synthesis of Cannabinoids

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dc.contributor.advisorMay, Jeremy A.
dc.contributor.committeeMemberDaugulis, Olafs
dc.contributor.committeeMemberHarth, Eva M.
dc.contributor.committeeMemberCzako, Barbara
dc.contributor.committeeMemberGuloy, Arnold M.
dc.creatorLuo, Jirong
dc.date.accessioned2022-08-09T02:19:00Z
dc.date.createdMay 2022
dc.date.issued2022-04
dc.date.updated2022-08-09T02:19:01Z
dc.description.abstract(–)-detla9-Tetrahydrocannabinol (THC) and cannabidiol (CBD) were synthesized via an organocatalyzed tandem enantioselective conjugate addition/enolate alkylation annulation with a novel ambiphilic trifluoroborate in 7 steps (longest linear steps; 10 steps overall with 23% yield for THC and 18% yield for CBD) from inexpensive commercially available starting materials. Both vinyl and aryl ambiphilic trifluoroborates were synthesized and showed great compatibility with various functional group, high yields, and excellent stereoselectivity. To demonstrate how these qualities will facilitate synthesizing THC and CBD analogs that were previously difficult to access with existing methods, we completed the synthesis of a novel benzo-fused A-ring analog of THC. Tandem reaction product containing all-carbon quaternary centers were also obtained with good to excellent enantioselectivity.
dc.description.departmentChemistry, Department of
dc.format.digitalOriginborn digital
dc.format.mimetypeapplication/pdf
dc.identifier.urihttps://hdl.handle.net/10657/10736
dc.language.isoeng
dc.rightsThe author of this work is the copyright owner. UH Libraries and the Texas Digital Library have their permission to store and provide access to this work. Further transmission, reproduction, or presentation of this work is prohibited except with permission of the author(s).
dc.subjectAmbiphilic organoboronates
dc.subjectConjugate addition
dc.subjectEnantioselective organocatalysis
dc.subjectCannabinoids
dc.titleDevelopment of Organocatalyzed Enantioselective Conjugate Addition and Application to the Total Synthesis of Cannabinoids
dc.type.dcmiText
dc.type.genreThesis
dcterms.accessRightsThe full text of this item is not available at this time because the student has placed this item under an embargo for a period of time. The Libraries are not authorized to provide a copy of this work during the embargo period.
local.embargo.lift2024-05-01
local.embargo.terms2024-05-01
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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