Stereoselective synthesis of sugar-fused (or 1,2-annulated) isochromans and isochromanones by using oxa-Pictet-Spengler reaction

A highly efficient stereoselective synthesis of sugar fused 1,2-annulated isochromans is reported by utilizing the oxa-Pictet-Spengler cyclization reaction. The process is found to be very general as both glucal and galactal derived C2-hydroxy-α-C-aryl glycosides lead to the target molecules in good...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2018-09, Vol.16 (37), p.8258-8262
Main Authors: Verma, Ashish Kumar, Chennaiah, Ande, Dubbu, Sateesh, Vankar, Yashwant D
Format: Article
Language:English
Subjects:
Aromatic compounds
Chemical synthesis
Crystallography
Glycosides
Stereoselectivity
Sugar
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Summary:A highly efficient stereoselective synthesis of sugar fused 1,2-annulated isochromans is reported by utilizing the oxa-Pictet-Spengler cyclization reaction. The process is found to be very general as both glucal and galactal derived C2-hydroxy-α-C-aryl glycosides lead to the target molecules in good yields. The utility of this strategy was extended to the synthesis of sugar fused isochromanones, which are bergenin type molecules. We report the utility of the oxa-Pictet-Spengler reaction in carbohydrates for stereoselective synthesis of sugar fused 1,2-annulated isochromans in good to excellent yields.
ISSN:1477-0520
1477-0539
DOI:10.1039/c8ob01698d