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

作者：Reddy B V Subba^*; Raju N Prudhvi; Someswarao B; Reddy B Jagan Mohan; Sridhar B; Marumudi Kanakaraju; Kunwar A C

来源：Organic and Biomolecular Chemistry, 2015, 13(16): 4733-4736.

DOI：10.1039/c5ob00376h

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 center dot OEt2 in dichloromethane at 0-25 degrees 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.

• 出版日期2015