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Novel iodine catalyzed diastereoselective synthesis of trans-2,6-disubstituted tetrahydro-2H-pyrans: synthesis of C1–C13 fragment of bistramide-A |
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| Authors: | Jhillu Singh Yadav Eppa GyanchanderAnand Kumar Mishra Peddapuram AdithyaSaibal Das |
| Affiliation: | Natural Products Chemistry Division, CSIR-Indian Institute of Chemical Technology, Tarnaka, Hyderabad 500 007, Andhra Pradesh, India |
| Abstract: | A new method for the stereoselective synthesis of trans 2.6-disubstituted tetrahydro-2H-pyrans has been developed involving iodine catalyzed allylation of tetrahydro-2H-pyranol with excellent trans selectivity. The method was also applied toward the construction of C1–C13 fragment of bistramide-A in 11 steps with 21.4% overall yield. |
| Keywords: | Tetrahydropyrans Iodine catalyzed allylation Non Evans aldol Isomerization Bistramide A |
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