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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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Supplementary files

Article information


Submitted
30 Dec 2017
Accepted
20 Feb 2018
First published
20 Feb 2018

Org. Chem. Front., 2018,5, 1320-1324
Article type
Research Article

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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