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Thomas Hoye receives Robert Robinson Award from RSC

Professor Thomas Hoye has been named the Royal Society of Chemistry's Robert Robinson Award winner for 2016. This award recognizes contributions to organic chemistry achieved and published by a researcher after having reached the age of 55.

Six eventual Nobel Laureates are among the illustrious list of the previous 30 winners of the Robert Robinson Award, inaugurated in 1964. Hoye will receive £2000, a medal, and a certificate during a lecture tour of UK universities in the upcoming year.

Hoye and his research group explore synthetic organic chemistry. Their studies are motivated principally either by what they make or how they make things. They synthesize compounds that have potential as active agents in, for example, new pharmaceuticals or organic light-emitting diodes (OLEDs). They also develop new reactions and new strategies that enable other synthetic chemists to improve the ways that they make the novel compounds that fuel their own research projects.

A major focus of Hoye's research is natural product chemical synthesis. His group has reported the total synthesis of eight structurally complex secondary metabolites in the last decade. The most recent of these—that of paracaseolide A [Nature Chemistry 2015]—is particularly noteworthy. This target had been synthesized five times since 2012 by Diels-Alder dimerizations, but previous investigators had not understood the intricate stereochemical features. He and a coworker fully unraveled these to reveal the likely biosynthesis of this naturally racemic compound: an exo-selective, bis-pericyclic reaction via a C2-symmetric TS followed by a remarkable, spontaneous epimerization—hence, a billing in a top journal to report the sixth DA-based synthesis!

An additional hallmark of Hoye's research program is its considerable breadth. His research encompasses the development of new synthetic methods; the development of new nuclear magnetic resonance-based strategies for determination of absolute and relative configurations [Nature Protocols 2007], including computational approaches [Nature Protocols 2014]; natural product structure determination [e.g., sea lamprey pheromones: Nature Chemical Biology 2005]; organometallic chemistry; polymer synthesis; development of sustainable materials from biorenewable resources; mechanistic organic chemistry; medicinal chemistry; spontaneous, non-enzyme-catalyzed events in the biosynthesis of natural products; and the development of new prodrugs and block polymer-based nanoparticles for drug and prodrug delivery.

Members of Hoye's research group have recently established that benzynes, arguably the most versatile of all the reactive intermediates in organic chemistry, can generally and practically be formed simply by heating appropriate triyne precursors [Nature 2012 and Nature Protocols 2013]. His group has termed this the hexadehydro-Diels–Alder (HDDA) reaction. They have also gained many new mechanistic insights about the ensuing in situ trapping reactions, which include a number of unprecedented classes of transformations—e.g., the aromatic ene reaction [Nature Chemistry 2014] and an alkane dehydrogenation reaction [Nature 2013]. This novel strategy for generating and trapping benzynes—HDDA cascades—provides a fundamentally new approach for the synthesis of useful new benzenoid compounds. The most recent outgrowth of this aspect of his program is the discovery of the pentadehydro-Diels–Alder (PDDA) reaction [Nature 2016].

Hoye received his bachelor’s and master’s degree from Bucknell University and earned his doctorate at Harvard University. He joined the University of Minnesota chemistry faculty in 1976. Among his recent awards are the 2015 Ernest Guenther Award in the Chemistry of Natural Products from the American Chemical Society and the 2014 Minnesota Award from the Minnesota Section of the American Chemical Society.

Hoye said: “The Robert Robinson Award, with its current intent to recognize significant research accomplishments achieved after reaching the age of 55, makes it, to my knowledge, unique among all awards in the chemical sciences – I applaud the RSC for its insight in establishing that criterion. More importantly, I am both thrilled and humbled to be named a recipient of this distinction, all the more so in view of the fact that the inaugural winner, R. B. Woodward, was my Ph.D. thesis adviser!”

For more information, visit Royal Society of Chemistry Prizes and Awards and the Robert Robinson Award