Tags: Organic Seminar

Ring-closing alkyne metathesis (RCAM) has received considerable attention over the last 20 years for its utility in synthesizing macrocycles[1]. While its more widely studied counterpart—alkene metathesis—has become a cornerstone of modern synthetic methodology for macrocycle formation, alkyne metathesis remains comparatively unexplored[2]. However, recent studies have highlighted the synthetic potential of cycloalkynes as versatile…

Late-stage functionalization, a transformative strategy in medicinal chemistry, enables precise modification of molecular frameworks through atom insertion, deletion, or exchange, offering rapid access to novel pharmacophores and enhancing drug discovery efforts. Nitrogen-containing heterocycles, such as indoles, pyrroles, and pyridines, are pivotal in pharmaceuticals.[1] Yet, existing methods for their diversification by nitrogen insertion…

Radical reactions have enjoyed widespread applications in both small molecule and macromolecule synthesis. However, it remains challenging to control the stereochemistry of radical transformations and to discover novel modes of radical catalysis which are not known in either organic chemistry or biochemistry. Combining synthetic chemistry, enzymology and protein engineering, our group advanced two new biocatalytic strategies for stereoselective…

Vinigrol, a natural product first isolated in 1987, has been studied extensively due to its unique structure and biological properties, including antihypertensive and platelet aggregation-inhibiting effects. Vinigrol has a unprecedented 6-6-8 tricyclic ring system with an axial four-carbon bridge, eight contiguous stereocenters, and a strained bicyclo[5.3.1]undecane ring similar to taxol. A combination of the complex structure and impressive…

The development of catalytic complexity-building transformations is essential to efficient synthetic design.1  The capacity of a single catalyst to induce multiple bond-forming events can facilitate the rapid construction of molecules of interest. Due to the abundance of heterocycles in pharmaceutical agents and natural products, heterocyclizations coupled to additional processes can be advantageous toward the synthesis of medicinally…

In 1964, the late Philip Eaton successfully synthesized cubane, a molecule once thought impossible. And then in 1992, Eaton announced that cubane should be considered more than novelty. He suggested that cubane could be used to replace benzene in pharmaceuticals to improve the pharmacokinetic properties of the parent drug. Following this announcement, cubane was only seen sporadically in the literature. But then thirty-four years later, this…

The photochemical activity of nitroarenes was first reported by Ciamician and Silber in 1901 when the unusual rearrangement of 2-nitrobenzaldehyde to 2-nitrosobenzoic acid was disclosed.1 The cyclization of photoexcited nitroarenes to ortho alkene and alkyne systems was described not long thereafter.2,3 Subsequent work by Ward4 and others5 defined the reactivity of photoexcited nitroarenes as an excitation, analogous to that of carbonyl groups…