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

Abstract

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.

Key words

arthrobotrisin A - Nozaki–Hiyama–Kishi coupling - Diels–­Alder reaction - Noyori reduction - Luche reduction - asymmetric synthesis

• References and Notes

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