A5087923573- Crystallization and Solubility Studies
- X-ray Diffraction in Crystallography
- Synthetic Organic Chemistry Methods
- Catalytic C–H Functionalization Methods
- Oxidative Organic Chemistry Reactions
- Chemical Synthesis and Analysis
- Bioactive Natural Diterpenoids Research
- Asymmetric Hydrogenation and Catalysis
- Traditional and Medicinal Uses of Annonaceae
- Plant-based Medicinal Research
- Cyclopropane Reaction Mechanisms
- Metal-Catalyzed Oxygenation Mechanisms
- Click Chemistry and Applications
- Metal complexes synthesis and properties
- Synthesis and Catalytic Reactions
- Plant biochemistry and biosynthesis
- Biological Activity of Diterpenoids and Biflavonoids
Florida State University
2018-2024
Tallahassee Orthopedic Clinic
2018
University of Alabama
2017
Metallo prodrugs that take advantage of the inherent acidity surrounding cancer cells have yet to be developed. We report a new class pH-activated metallo (pHAMPs) are activated by light- and pH-triggered ligand dissociation. These ruthenium complexes key characteristic hypoxic solid tumors (acidity) can exploited lessen side effects chemotherapy. Five type [(N,N)2Ru(PL)]2+ were synthesized, fully characterized, tested for cytotoxicity in cell culture (1A: N,N = 2,2′-bipyridine (bipy) PL,...
Abstract Methyl groups are ubiquitous in biologically active molecules. Thus, new tactics to introduce this alkyl fragment into polyfunctional structures of significant interest. With goal mind, a direct method for the Markovnikov hydromethylation alkenes is reported. This exploits degenerate metathesis reaction between titanium methylidene unveiled from Cp 2 Ti(μ‐Cl)(μ‐CH )AlMe (Tebbe's reagent) and unactivated alkenes. Protonolysis resulting titanacyclobutanes situ effects chemo‐, regio‐,...
A new polyene cyclization strategy exploiting β-ionyl derivatives was developed. Photoinduced deconjugation of the extended π-system within these chromophores unveils a contrathermodynamic that engages in Heck bicyclization to afford [4.4.1]-propellanes. This cascade improves upon limited regioselectivity achieved using existing biomimetic tactics and tolerates both electron-rich electron-deficient (hetero)aryl groups. The utility this approach demonstrated with diverted total synthesis...
Abstract Azetidines are valuable nitrogenous heterocycles. Herein, we disclose a strategy for the modular assembly of 3‐azetidines and related spirocyclic congeners featuring all‐carbon quaternary centers. This approach leverages titanacyclobutanes generated from ketones or alkenes. Halogenation these organotitanium species gives rise to functionalized alkyl dihalides that can be subsequently captured by amines afford azetidine building blocks. facilitated synthesis small molecule...
A stereoselective synthetic entry point to the 5-8-5 carbocyclic core of ophiobolins was developed. This strategy exploits chiral tertiary alcohol ophiobolin guide assmebly scaffold in a single step via photoinitiated cycloisomerization. Mechanistic insights into origin stereocontrol this reaction are described, as efforts elaborate resultant fused ring system pharmacophore A.
A 5-8-5 carbocyclic ring system forms the core of over 30 distinct natural products. Several members this family have gained attention for their diverse activity in cell culture. In these cases, biological function is mediated by arrangement substituents around a conserved nucleus. Despite potential applications privileged substructure medicinal chemistry, modular strategies its assembly are underdeveloped. Herein, we describe cycloisomerization reaction that framework directly. This...
Quaternary carbon centers pose a significant challenge in chemical synthesis. Harnessing the underexplored reactivity of titanacyclobutane intermediates, strategy to construct functionalized all-carbon quaternary from ketones is described. This methodology streamlines access wide variety azaspiro[3.n]alkanes that have emerged as valuable three-dimensional inputs for drug discovery.
Abstract Methyl groups are ubiquitous in biologically active molecules. Thus, new tactics to introduce this alkyl fragment into polyfunctional structures of significant interest. With goal mind, a direct method for the Markovnikov hydromethylation alkenes is reported. This exploits degenerate metathesis reaction between titanium methylidene unveiled from Cp 2 Ti(μ‐Cl)(μ‐CH )AlMe (Tebbe's reagent) and unactivated alkenes. Protonolysis resulting titanacyclobutanes situ effects chemo‐, regio‐,...
A concise, modular, and stereoselective synthetic entry point to the 5-8-5 carbocyclic core of ophiobolins is described. This strategy exploits chiral tertiary alcohol ophiobolin guide assmebly scaffold in a single step via photoinitiated isomerization. Mechanistic insights into origin stereocontrol this reaction are described, as efforts elaborate resultant polycycle pharmacophore A.
A versatile polyene cyclization strategy was developed that exploits conjugated -ionyl derivatives. Photomediated disruption of the extended -system within these chromophores unveils a contra-thermodynamic engages in Heck-type to afford [4.4.1]-propellanes. The connectivity overbred polycycles generated from this process is controlled by position requisite C–Br bond. Thus, compared conventional biomimetic cyclization, approach allows for complete control regiochemistry and facilitates...
A versatile polyene cyclization strategy was developed that exploits conjugated -ionyl derivatives. Photomediated disruption of the extended -system within these chromophores unveils a contra-thermodynamic engages in Heck-type to afford [4.4.1]-propellanes. The connectivity overbred polycycles generated from this process is controlled by position requisite C–Br bond. Thus, compared conventional biomimetic cyclization, approach allows for complete control regiochemistry and facilitates...