Issue 37, 2018

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

Abstract

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.

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

Supplementary files

Article information

Article type
Communication
Submitted
17 Jul 2018
Accepted
05 Sep 2018
First published
06 Sep 2018

Org. Biomol. Chem., 2018,16, 8258-8262

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

A. K. Verma, A. Chennaiah, S. Dubbu and Y. D. Vankar, Org. Biomol. Chem., 2018, 16, 8258 DOI: 10.1039/C8OB01698D

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