An Improved Synthesis of Conduritol A

Abstract

Abstract Recently Knapp and coworkers1 reported a highly stereoselective synthesis of the naturally occurring cyclitol conduritol A (1) from p-benzoquinone (2) in 39% overall yield using 9-[(benzyloxy)methoxy]-anthracene (3) as a protecting group (Scheme 1). Although regeneration of the olefinic bond in the product was achieved at room temperature via an oxyanion-accelerated2 retro Diels-Alder reaction, this step necessitated protection of the newly introduced groups.