A novel domino cyclization for the stereoselective synthesis of indeno[2,1-c]pyran and cyclopenta[c]pyran derivatives.

نویسندگان

  • B V Subba Reddy
  • N Prudhvi Raju
  • B Someswarao
  • B Jagan Mohan Reddy
  • B Sridhar
  • Kanakaraju Marumudi
  • A C Kunwar
چکیده

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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عنوان ژورنال:
  • Organic & biomolecular chemistry

دوره 13 16  شماره 

صفحات  -

تاریخ انتشار 2015