Mitchell Croatt

**Expertise: Organic Chemistry, Synthetic Methods Design and Development **Education: B.S., University of Minnesota, Twin Cities, 2002--Ph.D., Stanford University, 2007-- Postdoctoral Fellow, ETH-Zurich, 2008-2010

There are 21 included publications by Mitchell Croatt :

TitleDateViewsBrief Description
Alkynes and Azides: Not Just for Click Reactions. 2012 2030 We recently reported two unexplored reactivities of alkynes and azides. The first method reacts nucleophilic alkynes and electrophilic azides to synthesize sulfonyl-substituted 1,5-disubstituted-1,2,3-triazoles. The second method reacts electrophili...
Chemoselective fluorination and chemoinformatic analysis of griseofulvin: Natural vs fluorinated fungal metabolites 2017 153 [2017-2018 UNCG University Libraries Open Access Publishing Fund Grant Winner.] Griseofulvin is a fungal metabolite and antifungal drug used for the treatment of dermatophytosis in both humans and animals. Recently, griseofulvin and its analogues hav...
Decarboxylative and dehydrative coupling of dienoic acids and pentadienyl alcohols to form 1,3,6,8-tetraenes 2017 135 Dienoic acids and pentadienyl alcohols are coupled in a decarboxylative and dehydrative manner at ambient temperature using Pd(0) catalysis to generate 1,3,6,8-tetraenes. Contrary to related decarboxylative coupling reactions, an anion-stabilizing gr...
Development and Utilization of a Palladium-Catalyzed Dehydration of Primary Amides To Form Nitriles 2018 34 A palladium(II) catalyst, in the presence of Selectfluor, enables the efficient and chemoselective transformation of primary amides into nitriles. The amides can be attached to aromatic rings, heteroaromatic rings, or aliphatic side chains, and the r...
DFT Mechanistic Investigation of an Enantioselective Tsuji–Trost Allylation Reaction 2018 2 A comprehensive mechanistic examination of an asymmetric palladium-catalyzed Tsuji–Trost allylation reaction that identifies the enantioselective step was completed utilizing DFT computational tools and the nudged elastic band method. Key components ...
The Diene Effect: The Design, Development, and Mechanistic Investigation of Metal-Catalyzed Diene-yne, Diene-ene, and Diene-allene [2+2+1] Cycloaddition Reactions 2010 2170 Metal-catalyzed diene-yne, diene-ene, and diene-allene [2+2+1] cycloaddition reactions provide new methods for the facile construction of highly functionalized five-membered rings. These reactions can be conducted with a variety of substrate substitu...
Exploring the reactivity of 1,5-disubstituted sulfonyl-triazoles: Thermolysis and Rh(II)-catalyzed synthesis of a-sulfonyl nitriles 2013 1450 The reactivity of a series of 1,5-disubstituted sulfonyl-triazoles was explored using either thermolytic or metal-catalyzed conditions. Both the thermolysis and the Rh(II)-catalyzed reactions led to the synthesis of a-sulfonyl-nitriles, which presuma...
Hypervalent Iodonium Alkynyl Triflate Generated Phenylcyanocarbene and Its Reactivity with Aromatic Systems 2017 126 Phenylcyanocarbene was generated by the reaction of azide with a hypervalent iodonium alkynyl triflate and reacted in situ with 21 different carbocyclic and heterocyclic aromatic compounds. These reactions led to more complex products that frequently...
Isolation, Semisynthesis, Covalent Docking and Transforming Growth Factor Beta-Activated Kinase 1 (TAK1)-Inhibitory Activities of (5Z)-7-Oxozeaenol Analogues 2015 186 (5Z)-7-Oxozeanol and related analogues were isolated and screened to explore their activity as TAK1 inhibitors. Seven analogues were synthesized and more than a score of natural products isolated that examined the role that different areas of the mol...
Mechanistic Study of the Biomimetic Synthesis of Flavonolignan Diastereoisomers in Milk Thistle 2013 992 The mechanism for the biomimetic synthesis of flavonolignan diastereoisomers in milk thistle is proposed to proceed by single-electron oxidation of coniferyl alcohol, subsequent reaction with one of the oxygen atoms of taxifolin’s catechol moiety, an...
Metal-Catalyzed [2+2+1] Cycloadditions of 1,3-Dienes, Allenes, and CO 2006 1353 Step economy is a preeminent goal of synthesis.[1] It influences the length, efficiency, cost, time, separation, and environmental impact of a synthesis. Step economy is favored by the use of single, serial, or multicomponent reactions tha...
New reactions and step economy: the total synthesis of (±)-salsolene oxide based on the type II transition metal-catalyzed intramolecular [4 + 4] cycloaddition 2006 1688 Studies on the viability of the type II nickel-catalyzed intramolecular [4+4] cycloaddition of bis-dienes show that it is influenced by both diene substitution and geometry. Both E- and Z-isomers of 19 and 20 react, albeit at markedly different rates...
Probing the Role of the Mycosamine C2'-OH on the Activity of Amphotericin B 2011 1349 A synthetic route to a mycosamine donor was designed and provided access to a set of AmB derivatives targeted to probe the effect of the C2'-OH. It was determined that the configuration of the C2'-position is inconsequential but that O-methylation of...
Rhodium(I)-Catalyzed [2+2+1] Cycloadditions of 1,3-Dienes, Alkenes, and CO 2004 69 The evolution of organic synthesis relies heavily on the design and discovery of new reactions that generate structural complexity and value with step economy.1 Toward this end, we previously reported studies on new [4+4],2 [4+2],3 [5+2],4 and [6+2]5...
Rhodium(I)-Catalyzed [2+2+2+2] Cycloaddition of Diynes To Form Cyclooctatetraenes 2014 120 Unique reactivity of a rhodium catalyst in the presence of many different Lewis basic additives was observed and studied. In the absence of additives, it was observed that a selective [2+2+2] reaction to form benzene products occurred; however, in th...
Rhodium(I)-Catalyzed [2+2], [2+2+2], and [2+2+2+2] Cycloadditions of Dienes or Alkynes with a Bis-ene 2009 92 A novel metal-catalyzed, all-alkene [2+2+2] cycloaddition reaction involving a strained and conformationally restricted bis-ene and a diene is reported. Modification of the catalyst leads to competition with a diene-ene [2+2] reaction, and when an al...
Selective Formation of 1,5-Substituted Sulfonyl Triazoles Using Acetylides and Sulfonyl Azides 2011 1841 The reaction of acetylides with sulfonyl azides was found to selectively form 1,5-substituted sulfonyl triazoles. This reaction thus provides access to the regioisomeric product as compared to the popular copper-catalyzed azide–alkyne cycloaddition. ...
Semisynthesis, Cytotoxicity, Antiviral Activity, and Drug Interaction Liability of 7-O-methylated Analogues of Flavonolignans from Milk Thistle 2013 1391 Silymarin, an extract of the seeds of milk thistle (Silybum marianum), is used as an herbal remedy, particularly for hepatoprotection. The main chemical constituents in silymarin are seven flavonolignans. Recent studies explored the non-selective met...
Sequential Pd(0)-, Rh(I)-, and Ru(II)-Catalyzed Reactions in a Nine-Step Synthesis of Clinprost 2013 993 A step-economical synthesis of clinprost is reported that concludes with 3 different transition metal-catalyzed reactions: Pd-catalyzed decarboxylation with allylic rearrangement, Rh-catalyzed diene-ene [2+2+1] reaction, and Ru-catalyzed cross-metath...
Spiroscytalin, a New Tetramic Acid and Other Metabolites of Mixed Biogenesis from Scytalidium cuboideum 2015 157 Spiroscytalin (1), a new tetramic acid that possesses an uncommon spiro-ring fusion between a polyketide-derived octalin ring system and a 2,4-pyrrolidinedione, along with two known compounds, leporin B (2) and purpactin A (3), were isolated from a s...
Synthesis of Hypervalent Iodonium Alkynyl Triflates for the Application of Generating Cyanocarbenes 2013 121 The procedures described in this article involve the synthesis and isolation of hypervalent iodonium alkynyl triflates (HIATs) and their subsequent reactions with azides to form cyanocarbene intermediates. The synthesis of hypervalent iodonium alkyny...