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
Mini-Reviews in Organic Chemistry
Title: Chiro-Inositols in Organic Synthesis
Volume: 6 Issue: 1
Author(s): J. Singleton and J. O. Hoberg
Affiliation:
Keywords: D-chiro-inositol, L-chiro-inositol, pinitol, quebrachitol, asymmetric synthesis
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.
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Cite this article as:
Singleton J. and Hoberg O. J., Chiro-Inositols in Organic Synthesis, Mini-Reviews in Organic Chemistry 2009; 6 (1) . https://dx.doi.org/10.2174/157019309787316175
DOI https://dx.doi.org/10.2174/157019309787316175 |
Print ISSN 1570-193X |
Publisher Name Bentham Science Publisher |
Online ISSN 1875-6298 |
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