|Alkynes and Azides: Not Just for Click Reactions.
||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...
|The Diene Effect: The Design, Development, and Mechanistic Investigation of Metal-Catalyzed Diene-yne, Diene-ene, and Diene-allene [2+2+1] Cycloaddition Reactions
||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
||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...
|Metal-Catalyzed [2+2+1] Cycloadditions of 1,3-Dienes, Allenes, and CO
||Step economy is a preeminent goal of synthesis. 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
||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
||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...
|Selective Formation of 1,5-Substituted Sulfonyl Triazoles Using Acetylides and Sulfonyl Azides
||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
||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
||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...