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

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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

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Publication details

The article was received on 17 Jul 2018, accepted on 05 Sep 2018 and first published on 06 Sep 2018


Article type: Communication
DOI: 10.1039/C8OB01698D
Citation: Org. Biomol. Chem., 2018, Advance Article
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    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, Advance Article , DOI: 10.1039/C8OB01698D

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