| Title: | "Substitution dependent stereoselective construction of bicyclic lactones and its application to the total synthesis of pyranopyran, tetraketide and polyrhacitide A" |
| Author(s): | Subba Reddy BV; Biradar DO; Vikram Reddy Y; Yadav JS; Singarapu KK; Sridhar B; |
| Address: | "Centre for Semiochemicals, Hyderabad -500 007, India. basireddy@iict.res.in. Centre for Nuclear Magnetic Resonance, Hyderabad -500 007, India. Laboratory of X-ray Crystallography, CSIR-Indian Institute of Chemical Technology, Hyderabad -500 007, India" |
| ISSN/ISBN: | 1477-0539 (Electronic) 1477-0520 (Linking) |
| Abstract: | "A novel bicyclization strategy has been developed for the stereoselective synthesis of bicyclic lactones, i.e. 7-aryl or alkyl-2,6-dioxabicyclo[3.3.1]nonan-3-ones through a domino cyclization of (R)-3-hydroxyhex-5-enoic acid with an aldehyde in the presence of 10 mol% trimethylsilyltriflate under mild conditions. The salient features of this methodology are high yields, excellent selectivity, low catalyst loading and faster reaction times. This method has been successfully applied to the total synthesis of pyranopyran, tetraketide and polyrhacitide A" |
| Keywords: | "Aldehydes/chemical synthesis/chemistry Bridged Bicyclo Compounds, Heterocyclic/*chemical synthesis/chemistry Catalysis Cyclization Cyclohexanones/*chemical synthesis/chemistry Disaccharides/*chemical synthesis/chemistry Lactones/*chemical synthesis/chemis;" |
| Notes: | "MedlineSubba Reddy, B V Biradar, Dhanraj O Vikram Reddy, Y Yadav, J S Singarapu, Kiran Kumar Sridhar, B eng England 2016/10/08 Org Biomol Chem. 2016 Sep 21; 14(37):8832-8837. doi: 10.1039/c6ob01686c" |
