Toward the Stereoselective Synthesis of Arthrobotrisin A: Fragment Synthesis and Coupling Studies

Article abstract of DOI:10.1055/s-0036-1588950

A route towards the stereocontrolled synthesis of arthrobotrisin A based on a Nozaki-Hiyama-Kishi (NHK) coupling strategy was developed. Highlights of the fragment synthesis include enzyme-catalyzed kinetic resolution, Negishi carbometalation-iodination, quinone formation through oxidation with hypervalent iodine, chiral oxazaborolidine-catalyzed asymmetric Diels-Alder reaction with cyclopentadiene, regio- and stereoselective epoxidation, Noyori reduction, retro-Diels-Alder reaction, diastereoselective Luche reduction, and, finally, a Nozaki-Hiyama-Kishi (NHK) coupling of the vinyl iodide fragment.