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Discovery of MK-1439, an orally bioavailable non-nucleoside reverse transcriptase inhibitor potent against a wide range of resistant mutant HIV viruses.
The optimization of a novel series of non-nucleoside reverse transcriptase inhibitors (NNRTI) led to the identification of pyridone 36, now known as MK-1439, which is currently in clinical development for the treatment of HIV infection.
Convergent Kilogram-Scale Synthesis of Dual Orexin Receptor Antagonist
MK-6096 is an orexin receptor antagonist in clinical trials for the treatment of insomnia. Herein we describe its first kilogram-scale synthesis. Chirality on the α-methylpiperidine core was
Cu-catalyzed N-arylation of oxazolidinones: an efficient synthesis of the kappa-opioid receptor Agonist CJ-15161.
An efficient method for intermolecular N-arylation of oxazolidinones using catalytic copper in the presence of a bidentate ligand is reported and a short, scalable synthesis of CJ-15,161 is reported.
A Robust Kilo-Scale Synthesis of Doravirine
Doravirine is non-nucleoside reverse transcriptase inhibitor (NNRTI) currently in phase III clinical trials for the treatment of HIV infection. Herein we describe a robust kilo-scale synthesis for
Development of a Practical Synthesis of Stearoyl-CoA Desaturase (SCD1) Inhibitor MK-8245
A practical kilogram scale chromatography-free synthesis of stearoyl-CoA desaturase 1 (SCD1) inhibitor MK-8245 is described. The key features of this sequence include an efficient addition–eliminat...
Synthesis of 3-aminoisoxazoles via the addition-elimination of amines on 3-bromoisoxazolines.
A novel two-step procedure for the synthesis of 3-amino-5-substituted-isoxazoles is described. In the presence of a base, readily available 3-bromoisoxazolines react with amines to afford
Synthesis of highly functionalized bicyclo[m.n.1]alkanones via a cationic reaction cascade.
The acid-mediated Prins/ pinacol and the triple domino reactions Diels-Alder/Prins/pinacol were used to construct highly functionalized bicyclo-alkanones possessing various ring sizes from ketals 8-18 and 31a-c in 44-96% yields.
Conversion of systemically-distributed triazole-based stearoyl-CoA desaturase (SCD) uHTS hits into liver-targeted SCD inhibitors.
These efforts to convert a novel class of systemically-distributed potent triazole-based uHTS hits into liver-targeted SCD inhibitors as a means to circumvent chronic toxicity are described.
Phosphine-mediated [4 + 2] annulation of bis(enones): a Lewis base catalyzed "mock Diels-Alder" reaction.
Lewis-base-catalyzed cycloisomerization of bis(enones) to decalins has been demonstrated as an alternative to the traditional Lewis acid catalyzed Diels-Alder cycloaddition. In this process, a
Process Research and Scale-up of the κ-Opioid Receptor Agonist CJ-15,161 Drug Candidate
This account depicts strategies adopted during the development of the K-opioid receptor agonist CJ-15,161. While the original discovery synthesis was enabled for scale-up, concomitant process