Show simple item record

dc.contributor.authorBaidilov, Daler
dc.date.accessioned2020-01-22T14:25:53Z
dc.date.available2020-01-22T14:25:53Z
dc.identifier.urihttp://hdl.handle.net/10464/14612
dc.description.abstractThis thesis describes chemoenzymatic formal total syntheses of tetrodotoxin and a concise synthetic approach to daphenylline. Advanced intermediates for the syntheses of tetrodotoxin reported by the groups of Fukuyama, Alonso, and Sato were prepared. Key steps included toluene dioxygenase-mediated dihydroxylation of either iodobenzene or benzyl acetate and a [4+2] hetero-Diels-Alder cycloaddition/Kornblum–DeLaMare rearrangement sequence to construct a common enone intermediate. The resulting key enone was transformed into Fukuyama's intermediate in four steps, into Alonso's intermediate in six steps, and into Sato's intermediate in seven steps. Fukuyama’s route employed a highly stereoselective allyl cyanate-to-isocyanate rearrangement to install the nitrogen atom at C8a. This protocol was also successfully applied in designing a synthetic avenue to daphenylline. The ABC tricyclic skeleton of daphenylline was successfully constructed in just eight steps starting from readily available (S)-carvone.en_US
dc.language.isoengen_US
dc.publisherBrock Universityen_US
dc.subjecttetrodotoxinen_US
dc.subjectdaphenyllineen_US
dc.subjecttotal synthesisen_US
dc.titleChemoenzymatic Formal Total Syntheses of Tetrodotoxin and an Approach to Daphenyllineen_US
dc.typeElectronic Thesis or Dissertationen
dc.degree.namePh.D. Chemistryen_US
dc.degree.levelDoctoralen_US
dc.contributor.departmentDepartment of Chemistryen_US
dc.degree.disciplineFaculty of Mathematics and Scienceen_US
refterms.dateFOA2021-08-14T01:43:13Z


Files in this item

Thumbnail
Name:
Brock_Baidilov_Daler_2020.pdf
Size:
9.220Mb
Format:
PDF

This item appears in the following Collection(s)

Show simple item record