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Novel bilirubin and biliverdin congeners with propionic acids replaced by o -carboxyphenyl exhibit diastereomerism due to axial chirality about the carbon–carbon single bond linking the o -carboxyphenyl group to a pyrrole ring. Evidence for atropisomerism was found even in the monopyrrole...
Highly reactive zinc metal was prepared by electrolysis of a DMF solution containing naphthalene and a supporting electrolyte in a one-compartment cell fitted with a platinum cathode and a zinc anode. This reactive zinc was used for efficient transformation of ethyl 2-bromoacrylate into the...
Condensation of 1-(4,6-di- O -( tert -butyldimethylsilyl)-2,3-dideoxy-α- d - erythro -hex-2-enopyranosyl)-4-bromobenzene ( 2 ) with methyl 2-acetamidoacrylate in the presence of Pd(OAc) 2 , P(C 6 H 4 - O -CH 3 ) 3 , and AgNO 3 , afforded the unsaturated C -glycosyl enamido ester 3d in 80% yield....
A ring-closing metathesis (RCM) and a ring-opening metathesis (ROM) are combined in a domino process giving access to a variety of aza- and oxacyles, equipped with highly functionalized side chains, starting from readily accessible cyclopentenyl or cycloheptenyl ethers and amines. The role of...
The utilization of ultrasound radiation in the Baylis–Hillman reaction with several aldehydes (aromatics and aliphatics) and different α,β-unsaturated reactants is described. For all aldehydes tested, the utilization of ultrasound sources augmented the reaction rate and the chemical yields....
3-Aminopropionic acids (β-amino acids) are biologically active compounds of interest in medicinal and pharmaceutical chemistry. Twenty-one 3-amino-3-arylpropionic acids were synthesized via a facile one-pot synthesis. In addition, a series of mechanistic studies have been performed to optimize...
Two synthetic strategies to the COX-2 specific inhibitor 1 have been described that allowed its preparation in large quantities in 79% overall yield from ( S )-2-hydroxy-2-methylbutyric acid. These studies have led to the identification of an efficient resolution of (±)-2-hydroxy-2-methylbutyric...
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