Oxiranes are a class of cyclic ethers formed in abundance during the low-temperature combustion of hydrocarbons and biofuels from the unimolecular decomposition of hydroperoxyalkyl radicals (Q̇OOH). For example, ethyloxirane, cis-2,3-dimethyloxirane, and trans-2,3-dimethyloxirane are produced as intermediates during the oxidation of n-butane.

Conventional cross-coupling reactions typically involve the union of a nucleophilic and electrophilic coupling partner. In contrast, reductive (or cross-electrophile) coupling has recently emerged as an alternative approach in which two electrophilic partners can be coupled together. However, achieving cross-selectivity is an ongoing challenge for it necessitates chemoselective activation of one electrophile over the other.

Nucleophilic substitution reactions are at the heart of synthetic organic chemistry. While conventional strategies for conducting nucleophilic substitution reactions have been heavily studied, we hereby report the development of the novel photochemical approach to the induction of nucleophilic substitution reactions. This strategy employs a light-activated leaving group based on the 9-aryl-9-fluorene system. 9- fluorenol undergoes efficient photolysis of the C–O bond due to the stability of the aromatic 4π cyclic fluorenyl cation in the excited state.

Dithiodiketopiperazines or “DKP’s” is common motif that appears in various natural products. These natural products have been shown to display anti-viral or anti-tumor properties. Within the past two decades, an increasing number of natural products have been isolated containing a DKP core. Although synthetic strategy towards this core has been around since the 1960’s, there is still much innovation withing the area of DKP natural product total synthesis.

Antibody-drug conjugate (ADC) development has seen recent improvement through employment of targeted conjugate synthesis strategies. Methods that optimize delivery of antibodies, linkers, and conjugated drug compounds have emerged. Through these methods, higher drug conjugation density, increased linker stability, and lower unconjugated antibody concentrations can be achieved. Dual conjugation, a process by which two different conjugated drugs can be delivered, has become attractive for increased ADC potency.

Prof. Lawrence describes his research as “...primarily focused on the total synthesis of natural products, exploring new strategies and concepts in chemical synthesis, and developing new synthetic methodology.”

Natural products are organic secondary metabolites produced by all forms of life. In their native environment, natural products mediate intra- and interspecies communication. Bioinhibitory activities of natural products make them medicinally attractive– majority of clinically used drugs and pharmaceuticals are or are derived from natural products. The Agarwal laboratory seeks to understand how gene encoded enzymes construct natural product organic structures starting from simple biologically available starting materials.

As part of the the Spring 2022 Organic Seminar series, on January 27^th from 11:10 am we will host a virtual seminar by three representatives from Pfizer’s medicinal chemistry team:

Heme is an essential cofactor required for numerous biological reactions in the vast majority of organisms, and its biosynthesis is a complex process. Three heme biosynthetic pathways have been identified, with the most recent being the coproporphyrin dependent (CPD) pathway. In the CPD pathway, coproporphyrinogen III is oxidized to coproporphyrin, followed by iron insertion into the tetrapyrrole, forming coproheme¹.