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Studies Towards the Total Synthesis of 1-Deoxy-8-Demethyl Taxol

Title: Studies Towards the Total Synthesis of 1-Deoxy-8-Demethyl Taxol.
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Name(s): Koo, Ki Chul, 1972-, author
Holton, Robert A., professor directing dissertation
Reeves, Robert H., university representative
Krafft, Marie E., committee member
Dudley, Gregory B., committee member
Logan, Timothy M., committee member
Department of Chemistry and Biochemistry, degree granting department
Florida State University, degree granting institution
Type of Resource: text
Genre: Text
Issuance: monographic
Date Issued: 2009
Publisher: Florida State University
Place of Publication: Tallahassee, Florida
Physical Form: computer
online resource
Extent: 1 online resource
Language(s): English
Abstract/Description: The total synthesis towards 1-deoxytaxol analogs is described. The synthesis relies on new methods to install the C3-C4 bond and to achieve the tricyclic taxane ring skeleton. The first section describes the formation of the C3-C4 bond via a highly stereoselective one pot tandem enone formation and Michael addition reaction. The precursor for the tandem reaction was prepared from a taxane AB-ring intermediate which was developed for the synthesis of 1-deoxytaxol analogs in our laboratory. An elimination reaction provided a transient α,β-unsaturated ketone and the following intramolecular Michael addition reaction produced the desired C3-C4 bond-linked lactone as a single diastereomer. Section two describes the highly efficient C-ring closure by consecutive Michael addition and aldol condensation reaction of the previously obtained lactone. Indeed, Michael addition with acrolein led to the corresponding aldehyde adduct. The aldehyde was then employed for the intramolecular aldol condensation reaction to give the crucial tricyclic taxane intermediate. In the third section, preliminary studies describing the reactivity of the taxane intermediate towards the synthesis of 1,7-dideoxy-8-demethyltaxol are reported.
Identifier: FSU_migr_etd-2842 (IID)
Submitted Note: A Dissertation submitted to the Department of Chemistry and Biochemistry in partial fulfillment of the requirements for the degree of Doctor of Philosophy.
Degree Awarded: Fall Semester, 2009.
Date of Defense: August 19, 2009.
Keywords: Intermolecular Michael Addition, Intramolecular Michael Addition, Total Synthesis, 1, 7-Dideoxy, 8-Demethyl, 1-Deoxy, Taxol, Lactone Cleavage, Intramolecular Aldol Reaction
Bibliography Note: Includes bibliographical references.
Advisory Committee: Robert A. Holton, Professor Directing Dissertation; Robert H. Reeves, University Representative; Marie E. Krafft, Committee Member; Gregory B. Dudley, Committee Member; Timothy M. Logan, Committee Member.
Subject(s): Biochemistry
Biophysics
Molecular biology
Chemistry
Persistent Link to This Record: http://purl.flvc.org/fsu/fd/FSU_migr_etd-2842
Owner Institution: FSU

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Koo, K. C. (2009). Studies Towards the Total Synthesis of 1-Deoxy-8-Demethyl Taxol. Retrieved from http://purl.flvc.org/fsu/fd/FSU_migr_etd-2842