Chiro-Inositols in Organic Synthesis

J.      Singleton; J.   O.   Hoberg

Abstract

D- and L-chiro inositols are the enantiomeric pair of carbocyclic carbohydrates obtained from naturally occurring pinitol and quebrachitol. As apposed to well-known sugars that contain a ring oxygen, an anomeric carbon and a primary alcohol, these carbohydrates are comprised of only six secondary alcohols, no ring oxygen and hence no anomeric position. This leads to an inherent complexity and their use as synthetic precursors, chiral ligands and chiral auxiliaries have grown as methods to overcome this complex nature have been developed. Strategies for selective alcohol protection, synthetic transformations, their use in asymmetric synthesis and NMR spectroscopy are discussed in this mini-review.

Keywords: D-chiro-inositol, L-chiro-inositol, pinitol, quebrachitol, asymmetric synthesis