Mark D. Ferguson

Highly efficient and versatile synthesis of libraries of constrained β-strand mimetics

The general approach of using a bicyclic template to produce inhibitors of the protease superfamily of enzymes has been investigated. The Diels-Alder cycloaddition reaction on solid support has been found to be highly efficient for the synthesis of libraries of compounds that mimic the β-strand secondary structure of proteins. Several potent and selective inhibitors of proteases have been discovered.

Heterocumulenes as 2π partners in metal-promoted [6π+2π] cycloaddition reactions

Abstract Alkyl and aryl substituted isocyanates and ketenes have been shown to be useful 2π partners in photoinitiated chromium(O)-promoted [6π+2π] cycloaddition reactions.

The development of hydrazide γ-turn mimetics

Abstract Monte Carlo calculations show a classical γ-turn in a family of metabolites known as the malformins. This led to the synthesis of epimeric seven-membered ring γ-turn mimetics starting from leucine. NMR temperature coefficient studies were also performed.

Transition metal promoted higher-order cycloaddition reactions. [6+2] cycloaddition of a fischer carbene complex with tricarbonyl(cycloheptatriene) chromium(0)

Abstract Photolytic reaction of pentacarbonyl [(methoxy)(methyl)carbene] chromium(0) with tricarbonyl(cycloheptatriene) chromium(0) afforded an isomeric mixture of bicyclo[4.2.1]nonanone products.

Synthesis of 3-alkoxyazetidin-2-ones: Dipeptide mimics

Abstract Several dipeptide mimics, 3-alkoxyazetidin-2-ones, were prepared in a diastereoselective fashion by the direct displacement of a scalemic triflate with 3-hydroxyazetidin-2-ones. The scope and limitation are presented.