Natural Products Synthesis via Organoiron Methodology
Funding Agency: National Science Foundation-Division of Chemistry
Award number: 0848870
Investigators:
- William A. Donaldson
NSF programs: Methodology
Abstract
This project will continue work to develop new organometallic methodology to prepare C-C bonds in a stereoselective fashion, and applications of this methodology. In particular, the preparation of (2-alkenyl-3-pentene-1,5-diyl)iron complexes and their transformation into vinylcyclopropanes and divinylcyclopropanes will be targeted. The divinylcyclopropanes are likely to undergo rearrangement to cycloheptadienes. These reactions will be applied to the synthesis of beta-aminocyclopropanecarboxylic acids and frondosin A, an inhibitor of the binding of interleukin-8 to its receptor.
With this award, the Organic and Macromolecular Chemistry Program is supporting the research of Professor William A. Donaldson of the Department of Chemistry at Marquette University. Professor Donaldson's research efforts revolve around the development of organometallic methodology for the formation of cyclopropanes and cycloheptadienes, structural motifs present in a variety of biologically relevant molecules. Successful development of the methodology will have an impact on synthesis in the pharmaceutical and agricultural industries.
Link to NSF award abstractArticles
A Shortened Synthesis of Optically Pure Tricarbonyl[methyl (2E,4E)-6-oxo-2,4-hexadienoate]Iron Leading to Improved Yield, Rajesh K. Pandey, Sergey Lindeman, and William A. Donaldson
Generation of Molecular Complexity from Cyclooctatetraene: Preparation of Optically Active Protected Aminocycloheptitols and Bicyclo[4.4.1]undecatriene, Mohamed F. El-Mansy, Anobick Sar, Sergey V. Lindeman, and William A. Donaldson
Generation of Molecular Complexity from Cyclooctatetraene Using Dienyliron and Olefin Metathesis Methodology, Mohamed F. El-Mansy, Anobick Sar, Subhabrata Chaudhury, Nathaniel J. Wallock, and William A. Donaldson
Probing the Human Estrogen Receptor-Alpha Binding Requirements for Phenolic Mono- and di-Hydroxyl compounds: A Combined Synthesis, Binding and Docking Study, Christopher McCullough, Terrence S. Neumann, Jayapal Reddy Gone, Zhengjie He, Christian Herrild, Julie Lukesh, Rajesh K. Pandey, William A. Donaldson, and Daniel S. Sem
Reactivity of acyclic (pentadienyl)iron(1+) cations: Synthetic studies directed toward the frondosins, Do W. Lee, Rajesh K. Pandey, Sergey V. Lindeman, and William A. Donaldson
Recent Applications of Acyclic (Diene)iron Complexes and (Dienyl)iron Cations in Organic Synthesis, William Donaldson and Subhabrata Chaudhury
Recent Applications of the Simple Hydrocarbon Cyclooctatetrene as a Starting Material for Complex Molecule Synthesis, Kevin W. Glaeske and William A. Donaldson
Synthesis of Hydroxy- and Polyhydroxy-Substituted 1,3-Diaminocyclohexanes, Anobick Sar, Sergey Lindeman, and William A. Donaldson
Spectral Data
Spectral Data for "Generation of Molecular Complexity from Cyclooctatetraene: Preparation of Optically Active Protected Aminocycloheptitols and Bicyclo[4.4.1]undecatriene", Mohamed F. El-Mansy, Anobick Sar, Sergey V. Lindeman, and William A. Donaldson
Spectral Data for "Probing the human estrogen receptor-alpha binding requirements for phenolic mono- and do-hydroxyl compounds: A combined synthesis, binding and docking study", Christopher McCullough, Terrence S. Neumann, Jayapal Reddy Gone, Zhengjie He, Julie Lukesh, Rajesh K. Pandey, William A. Donaldson, and Daniel S. Sem
Spectral Data for "Reactivity of acyclic (pentadienyl)iron(1+) cations: Synthetic studies directed toward the frondosins", Do W. Lee, Rajesh K. Pandey, Sergey V. Lindeman, and William A. Donaldson
Spectral Data for "Synthesis of Cyclopropanes via Organoiron Methodology: Stereoselective Preparation of Bi(cyclopropyl)s", Rajesh K. Pandey, Sergey V. Lindeman, and William A. Donaldson
Sprectral data for "Generation of Molecular Complexity from Cyclooctatetraene Using Dienyliron and Olefin Metathesis", Mohamed F. El-Mansy, Anobick Sar, Subhabrata Chaudhury, Nathaniel J. Wallock, and William A. Donaldson