Novel iodine catalyzed diastereoselective synthesis of trans-2,6-disubstituted tetrahydro-2H-pyrans: synthesis of C1–C13 fragment of bistramide-A

Yadav, Jhillu Singh ; Gyanchander, Eppa ; Mishra, Anand Kumar ; Adithya, Peddapuram ; Das, Saibal (2013) Novel iodine catalyzed diastereoselective synthesis of trans-2,6-disubstituted tetrahydro-2H-pyrans: synthesis of C1–C13 fragment of bistramide-A Tetrahedron Letters, 54 (44). pp. 5879-5882. ISSN 0040-4039

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Official URL: http://doi.org/10.1016/J.Tetlet.2013.08.085

Related URL: http://dx.doi.org/10.1016/J.Tetlet.2013.08.085

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.

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