title: A novel domino cyclization for the stereoselective synthesis of indeno[2,1-c]pyran and cyclopenta[c]pyran derivatives.
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.
authors: Natural Product Chemistry, CSIR-Indian Institute of Chemical Technology, Hyderabad-500 007, India. basireddy@iict.res.in.
authors: B V
authors: BV
authors: Subba Reddy
authors: N
authors: N
authors: Prudhvi Raju
authors: B
authors: B
authors: Someswarao
authors: B Jagan
authors: BJ
authors: Mohan Reddy
authors: B
authors: B
authors: Sridhar
authors: Kanakaraju
authors: K
authors: Marumudi
authors: A C
authors: AC
authors: Kunwar
mesh_terms: D000893:Anti-Inflammatory Agents / Q000737:chemistry; D001578:Benzopyrans / Q000737:chemistry; D001688:Biological Products; D002626:Chemistry, Pharmaceutical; D002855:Chromatography, Thin Layer; D003500:Cyclization; D000431:Ethanol / Q000737:chemistry*; D006416:Hematoxylin / Q000737:chemistry; D007192:Indenes / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D008752:Methylene Chloride / Q000737:chemistry; D008968:Molecular Conformation; D015394:Molecular Structure; D010975:Platelet Aggregation Inhibitors / Q000737:chemistry; D011714:Pyrans / Q000737:chemistry*; D012997:Solvents / Q000737:chemistry; D017550:Spectroscopy, Fourier Transform Infrared; D013237:Stereoisomerism; D013696:Temperature
chemical_list: C000599525:2-(2-(hydroxymethyl)-1-methylene-2,3-dihydro-1H-inden-2-yl)ethanol; D000893:Anti-Inflammatory Agents; D001578:Benzopyrans; D001688:Biological Products; D007192:Indenes; D010975:Platelet Aggregation Inhibitors; D011714:Pyrans; D012997:Solvents; C000599526:indeno(2,1-c)pyran; D000431:Ethanol; D008752:Methylene Chloride; C044362:brazilin; D006416:Hematoxylin