Department of Chemistry
These digital collections include theses, dissertations, faculty publications, and datasets from the Department of Chemistry.
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Concise enantioselective synthesis of (+)-FR66070 and (+)-FR900482 and the synthesis and biochemical studies of a photo-triggered FR900482 mitosene progenitor
The total synthesis of the natural products (+)-FR66979 and (+)-FR900482 is presented. The synthesis features a novel dimethyldioxirane-mediated reaction for construction of the hydroxylamine hemiketal functionality and ... -
Studies on the total synthesis of putative intermediates in the biosynthesis of taxol
The exploration of several strategies for the synthesis of taxoids useful for studying the biosynthesis of taxol is presented. The approaches described include attempts to access the taxane carbon skeleton through closure ... -
Asymmetric total syntheses of (+)- and (-)-spirotryprostatins A and B
The first published total synthesis of (+)- and (-)-spirotryprostatin B is presented. The synthesis features an asymmetric azomethine ylide [1,3]-dipolar cycloaddition reaction. Additionally, a Barton-modified Hunsdiecker ... -
Asymmetric synthesis of (2S,3R)-capreomycidine and the total synthesis of capreomycin IB, The
An efficient and asymmetric synthesis of the non-proteinogenic amino acid (2S,3R)-capreomycidine is presented. The synthesis features a novel aluminum enolate-aldimine reaction with a chiral glycinate, which sets both ... -
Synthesis and biological evaluation of potential DNA cross-linking agents based on pyrrolizidine alkaloids
DNA cross-linking agents represent one of the most potent categories of antitumor agents. Pyrrolizidine alkaloids are an abundant class of biologically active natural products. These alkaloids display high levels of DNA ... -
Total synthesis of (-)-tetrazomine and biochemical studies
The total synthesis of (-)-tetrazomine is presented in which the relative and absolute stereochemistry of the natural product has been determined. The synthesis features a unique iminium cyclization followed by a 1,3-dipolar ... -
Studies on the biosynthesis of paraherquamide A and the total synthesis of (±) VM55599
Studies that partially elucidate the biosynthetic pathway of the heptacyclic fungal metabolite, Paraherquamide A are presented. Through biosynthetic feeding experiments with stable isotope labeled compounds, it was determined ... -
Towards the total synthesis of 14-acetoxygelsenicine and synthesis of largazole analogs
Herein are documented our efforts in two projects, beginning with studies towards the total synthesis of 14-acetoxygelsenicine. We have developed different strategies towards this complex natural product, wherein we have ... -
Progress toward an asymmetric total synthesis of the Stemona alkaloid tuberostemoninol
Presented herein is a twenty-five linear step synthetic progress toward an asymmetric total synthesis of the Stemona alkaloid tuberostemoninol. A diastereoselective intramolecular Pauson-Khand reaction of a glycinate ... -
Progress towards the enhanced synthesis of FK228 and analogs; and the total synthesis of Largazole-Azumamide hybrid
Progress towards an improved synthesis of HDAC inhibitor FK228 and work towards the completion of FK228 and Largazole Azumamide hybrids are presented. Through investigation of previous syntheses of FK228, a synthesis aimed ... -
Total synthesis of (-)-paraherquamide A, The
The first stereocontrolled total synthesis of (-)-paraherquamide A is described in 48 chemical steps. The synthesis is a convergent one, starting from ethyl glycinate, ethyl acrylate and vanillin. The longest linear route ... -
Progress towards proposed biosynthetic intermediates of stephacidin A
Progress towards three potential biosynthetic intermediates of stephacidin A are presented. The first precursor has a 7-prenylated indole ring system, the second precursor has a 7-prenyl 6-hydroxy indole ring system, and ... -
Mitomycin alkaloids: synthetic studies
Documented herein are efforts towards the first asymmetric total synthesis of the mitomycin family of natural products. Methods have been developed that efficiently construct eight-membered ring precursors of the natural ... -
Asperparaline A: biosynthetic studies and synthetic efforts
Asperparaline A, a fungal metabolite isolated from Aspergillus japonicus, is of interest due to anthelmintic activity and structural similarities to the paraherquamides and brevianamides owing to the presence of bicyclo ... -
Studies towards the total synthesis of spiroquinazoline
Presented herein is the synthesis of a key intermediate in the total synthesis of spiroquinazoline. By using N-Boc-serine as starting material, an efficient methodology has been developed to synthesize two types of ... -
Studies towards the total synthesis of (-)-lemonomycin
An asymmetric synthesis of the tetracyclic core of (-)-lemonomycin is presented. It features an efficient route towards a highly versatile tetrahydroisoquinoline intermediate, in which a diastereoselective Pictet-Spengler ... -
Studies towards the biomimetic synthesis of the stephacidin family of natural products and the concise and versatile synthesis of d,l-brevianamide B, C-12A-epi-malbrancheamide and structurally related analogs
The total synthesis of stephacidin A, avrainvillamide and stephacidin B was envisioned to proceed through a biomimetic intramolecular Diels-Alder cylcoaddition. The Diels-Alder precursor was thought to come from the coupling ... -
Concise total synthesis of the TMC-95A and TMC-95B proteasome inhibitors, A
A concise total synthesis of the TMC-95A/B proteasome inhibitors is presented. The synthesis features the use of an L-serine derived E-selective modified Julia olefination reaction that ultimately controls the stereochemical ... -
Concise asymmetric syntheses of the cylindrospermopsin alkaloids
Presented herein is a concise 18 step asymmetric synthesis of the hepatotoxic cyanobacterial alkaloids cylidrospermopsin, 7-epi-cylindrospermopsin, and the purported structure of 7-deoxycylindrospermopsin. Born from a ...
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