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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 ...
Total Synthesis of Aflastatin A
(2013-08-21)
The syntheses of aflastatin A and its C3-C48 degradation fragment are described. The syntheses feature several complex diastereoselective fragment couplings, including a C35-C36 anti-Felkin-selective boron-mediated oxygenated ...
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 ...
I. Engaging Cationic Intermediates in Asymmetric Catalysis: Enantioselective Reactions of Carbenium Ions and N,N-Dialkyliminium Ions II. Enantioselective Catalysis of the Cope-Type Hydroamination by H-Bond Donors
(2013-09-16)
The research described here explores the ability of dual H-bond donor catalysts to induce asymmetry in a variety of synthetically useful transformations that proceed via diverse reactive intermediates. In Chapters 1-3, ...
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 ...
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 ...
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 ...
Elucidation of the Cation−π Interaction in Small-Molecule Asymmetric Catalysis
(2013-10-14)
The cation–π interaction has been long-established to play an important role in molecular recognition, supramolecular chemistry, and molecular biology. In contrast, its potential application in small-molecule ...
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 ...