Total synthesis of myristinins A–F and 3′-hydroxy-5,7-dimethoxy-4-O-2′-cycloflavan by iterative generation of o-quinone methides

Abstract

An iterative generation of o-quinone methides (o-QMs) and [4+2] cycloaddition followed by inter/intra-molecular Michael addition in a cascade sequence gave expedient access to total synthesis of myristinins A–F and 3′-hydroxy-5,7-dimethoxy-4-O-2′-cycloflavan and their analogues, respectively. This cascade sequence cyclisation successfully provided the shortest route to the gram-scale synthesis of the myristinin family, including the first total synthesis of myristinin D–F and 3′-hydroxy-5,7-dimethoxy-4-O-2′-cycloflavan.