Totally Synthetic Routes to the Higher Monosaccharides

✍ Scribed by Prof. Samuel J. Danishefsky; Michael P. DeNinno

• Book ID: 102726296
• Publisher: John Wiley and Sons
• Year: 1987
• Tongue: English
• Weight: 714 KB
• Volume: 26
• Category: Article
• ISSN: 0044-8249
• DOI: 10.1002/anie.198700151

✦ Synopsis

The evolution of a strategy to synthesize the title compounds is described. Three principal developments allowed realization of this goal: (1) the attainment of high margins of diastereofacial selectivity and regioselectivity in the construction of pyranoid systems via the Lewis acid-catalyzed cyclocondensation reaction of activated dienes and aldehydes ; (2) the exploitation of stereoselective reactions for functionalization of the pyranoid matrix; and ( 3 ) the discovery of stereoselective reactions for extending the chiral biases of pyranoid systems to newly emerging stereogenic centers on side chains. The coordination of these components in the synthesis of target systems of high biological interest is described.