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Progress Toward the Total Synthesis of Vinigrol and Hibarimicin B
(2014-02-25)
Vinigrol is a structurally unique diterpenoid natural product featuring a tricyclo[4.4.4.0.4a,8a]tetradecene carbon skeleton containing eight contiguous stereocenters and a challenging oxygenation pattern. Vinigrol has ...
The Role of Catalyst-Catalyst Interactions in Asymmetric Catalysis with (salen)Co(III) Complexes and H-Bond Donors
(2013-10-14)
In asymmetric catalysis, interactions between multiple molecules of catalyst can be important for achieving high catalyst activity and stereoselectivity. In Chapter 1 of this thesis, we introduce catalyst-catalyst interactions ...
On the Development of Pseudoephenamine and Its Applications in Asymmetric Synthesis
(2014-06-06)
Pseudoephedrine is well established as a chiral auxiliary in the alkylation of amide enolates to form tertiary and quaternary carbon stereocenters. However, due to its facile transformation into the illegal narcotic ...
Total Synthesis of Hyperforin
(2013-10-17)
Hyperforin is the component of the medicinal herb St. John's Wort (Hypericum perforatum) responsible for its antidepressant activity. It works by blocking the reuptake of a variety of neurotransmitters through a unique ...
Total Syntheses of Fastigiatine and the Hibarimicin Aglycons
(2013-10-07)
Part one of this two-part thesis describes my efforts toward the total syntheses of the complex polycyclic alkaloids himeradine A and fastigiatine, which are members of the Lycopodium family of natural products. A cascade ...
Component-Based Syntheses of Trioxacarcins
(2014-06-06)
The trioxacarcins are structurally complex, highly oxygenated bacterial isolates that potently inhibit the growth of human cancer cells in culture as a consequence of their ability to alkylate guanosine residues of duplex ...
I. Completion of a Total Synthesis of Peloruside A. II. Studies toward the Total Synthesis of Spiro-Prorocentrimine
(2013-03-05)
I. Completion of a Total Synthesis of Peloruside A: The completion of a 22 step synthesis of the marine natural product peloruside A is presented. The second generation strategy cuts 10 steps from longest linear sequence ...
Multiplicative Expansion of the Pool of Fully Synthetic Tetracycline Antibiotics
(2013-03-05)
This thesis describes the development of chemical pathways for the preparation of more than 80 novel fully synthetic tetracyclines with structural variability at positions C5 and C5a. Progress toward the synthesis of ...
Late-Stage Fluorination with \(^{18}F\)
(2013-03-19)
Positron emission tomography (PET) is a powerful, non-invasive in vivo imaging technique used for diagnostics and drug development. The synthesis of \(^{18}F\)-PET tracers is challenging due to the short half-life of the ...
I. Enantioselective Acylation of Silyl Ketene Acetals through Fluoride Anion-Binding Catalysis II. Development of a Practical Method for the Synthesis of Highly Enantioenriched Trans-1,2-Amino Alcohols
(2013-08-21)
A highly enantioselective acylation of silyl ketene acetals with acyl fluorides was developed to generate useful α,α-disubstituted butyrolactone products in high yield and excellent enantioselectivities. This transformation ...