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We report the chemical synthesis of six oxidized derivatives of MK-0476 (Montelukast, L-706631), which have been key tools in the identification of its metabolites. We have prepared three diastereoisomeric pairs of potential oxidative metabolites of MK-0476, starting from the (S)-hydroxy ester 7 in 10 and five steps, and starting from MK-0476 itself in one step. The key benzylic hydroxyl of 1 and 2 was introduced by a bromination and saponification reaction sequence. In the case of the hydroxyl of 3 and 4, the key step was the addition of a hydroxymethyl carbanion equivalent on ketone 20. The two sulfoxide 5 and 6 were prepared by a direct oxidation of MK-0476 with m-chloroperbenzoic acid.

Sodium salts of indoles have been found to open α-1,2-anhydrosugars with inversion yielding indole-β-N-glycosides. This methodology constitutes a concise route from glycals to the biologically active indole-N-glycosides. An application to the total synthesis of rebeccamycin is described

We have suggested that the elements of a molecular construction set can be made by linking 2-pyridones with rigid spacers to create compounds that form predictable, strongly hydrogen-bonded duplexes. In this paper we describe the aggregation of similar dipryridones linked by flexible spacers