Total synthesis of gabosines via an iron-catalyzed intramolecular tandem aldol process

Abstract

Several gabosines, belonging to polyhydroxy-cyclohexenone and cyclohexanone class of natural products, are synthesized in various stereoforms using an intramolecular iron-catalyzed tandem aldol process. The reaction, which starts from vinylic pyranoses, is compatible with two different OH protecting groups (acetyl and benzyl). Further, like the Ferrier carbocyclisation, it is not sensitive to the stereochemistry of sugar molecules used as precursors: six different gabosine-type molecules have been prepared by this route starting from d-Glucose, d-Mannose, and d-Galactose derivatives.