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  • Title: A novel domino cyclization for the stereoselective synthesis of indeno[2,1-c]pyran and cyclopenta[c]pyran derivatives.
    Author: Subba Reddy BV, Prudhvi Raju N, Someswarao B, Mohan Reddy BJ, Sridhar B, Marumudi K, Kunwar AC.
    Journal: Org Biomol Chem; 2015 Apr 28; 13(16):4733-6. PubMed ID: 25804904.
    Abstract:
    A novel bicyclization of 2-(2-(hydroxymethyl)-1-methylene-2,3-dihydro-1H-inden-2-yl)ethanol with aldehydes in the presence of 10 mol% BF3·OEt2 in dichloromethane at 0-25 °C affords the biologically relevant indeno[2,1-c]pyran scaffolds in good yields with high selectivity. Similarly the bicyclization of 2-(1-(hydroxymethyl)-2-methylenecyclopentyl)ethanol with aldehydes generates the corresponding cyclopenta[c]pyran derivatives under similar conditions. This method is very useful to produce hematoxylin and brazilin like scaffolds.
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