Enantioselective Total Syntheses of Preussomerins: Control of Spiroacetal Stereogenicity by Photochemical Reaction of a Naphthoquinone through 1,6-Hydrogen Atom Transfer

Abstract

We report the enantioselective total syntheses of preussomerins EG1, EG2, and EG3. The key transformation is a stereospecific photochemical reaction involving 1,6-hydrogen atom transfer to achieve retentive replacement of a C−H with a C−O bond, enabling otherwise-difficult control of the spiroacetal stereogenic center.