Short practical synthesis of (3R,4R,5R,6R)-tetrahydroxyazepane and (3S,4S,5S,6S )-tetrahydroxyazepane from D- and L-chiro-inositol, respectively

Abstract

The polyhydroxylated azepanes (3R,4R,5R,6R)-tetrahydroxyazepane (−)-1 and (3S,4S,5S,6S)-tetrahydroxyazepane (+)-1 are synthesised from D-and L-chiro-inositol, respectively. Key transformations in the reaction sequence include a glycol-fission reaction with sodium metaperiodate supported on silica gel and the double reductive amination of a manno-1,6-dialdehyde derivative. This work represents the first synthesis of tetrahydroxyazepanes from inositols.