Benjamin Marcune

Development of a practical, asymmetric synthesis of the hepatitis C virus protease inhibitor MK-5172.

The development of a practical, asymmetric synthesis of the hepatitis C virus (HCV) protease inhibitor MK-5172 (1), an 18-membered macrocycle, is described.

A Practical Process for the Preparation of Azetidine-3-carboxylic Acid

Abstract A practical and convenient synthesis of azetidine-3-carboxylic acid (1) that proceeded in 55% overall yield from commercially available diethylbis(hydroxymethyl)malonate (3) is reported. Azetidine ring-formation was achieved in high yield by cyclization of bistrifiate of the diol (3) and benzylamine. Decarboxylation under carefully pH-controlled conditions gave the mono acid azetidine that was hydrogenated to give the title compound.

Synthesis of antifungal glucan synthase inhibitors from enfumafungin.

An efficient, new, and scalable semisynthesis of glucan synthase inhibitors 1 and 2 from the fermentation product enfumafungin 3 is described. The highlights of the synthesis include a high-yielding ether bond-forming reaction between a bulky sulfamidate 17 and alcohol 4 and a remarkably chemoselective, improved palladium(II)-mediated Corey-Yu allylic oxidation at the highly congested C-12 position of the enfumafungin core. Multi-hundred gram quantities of the target drug candidates 1 and 2 were prepared, in 12 linear steps with 25% isolated yield and 13 linear steps with 22% isolated yield, respectively.

Intramolecular aromatic 1,5-hydrogen transfer in free radical reactions. II. Rearrangement of iodobenzophenones

Abstract Products derived from the homolysis of the aromatic CI bond of ortho -iodobenzophenones by photolysis or tributyltin radicals indicate 1,5-hydrogen migration. The reactions include iodine migration, hydrogen abstraction and arylation.

CCDC 1417569: Experimental Crystal Structure Determination

Related Article: John Y. L. Chung, Benjamin Marcune, Hallena R. Strotman, Rositza I. Petrova, Jeffrey C. Moore, Peter G. Dormer|2015|Org.Process Res.Dev.|19|1418|doi:10.1021/acs.oprd.5b00259