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Issue 8, 2018
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Tandem Prins-type cyclization for the stereoselective construction of fused polycyclic ring systems

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Abstract

A novel strategy has been developed for the synthesis of fused tetrahydrofuro[3,2-c]pyrano[2,3-b]chromene derivatives through the condensation of 2-hydroxybenzaldehydes with 2-(3,4-dihydro-2H-pyran-5-yl)ethan-1-ol in the presence of 20 mol% TMSOTf in dichloromethane at 25 °C. Similarly, the coupling of aromatic aldehydes with 2-(3,4-dihydro-2H-pyran-5-yl)ethan-1-ol provides the corresponding hexahydro-4H-furo[3′,2′:2,3]indeno[1,2-b]pyran derivatives in good yields with high diastereoselectivity. It is a modular approach for the rapid construction of polycyclic architectures in a single step. These cyclic frameworks are an integral part of the structure of many natural products.

Graphical abstract: Tandem Prins-type cyclization for the stereoselective construction of fused polycyclic ring systems

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Publication details

The article was received on 30 Dec 2017, accepted on 20 Feb 2018 and first published on 20 Feb 2018


Article type: Research Article
DOI: 10.1039/C7QO01164D
Citation: Org. Chem. Front., 2018,5, 1320-1324
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    Tandem Prins-type cyclization for the stereoselective construction of fused polycyclic ring systems

    B. Someswarao, R. K. P., B. J. M. Reddy, S. B. and V. S. R. B., Org. Chem. Front., 2018, 5, 1320
    DOI: 10.1039/C7QO01164D

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