Yadav, J. S. ; Sunitha, V. ; Subba Reddy, B. V. ; Das, P. P. ; Gyanchander, E. (2008) InBr3-catalyzed stereoselective synthesis of trans-2,6-disubstituted 3,6-dihydro-2H-pyrans Tetrahedron Letters, 49 (5). pp. 855-857. ISSN 0040-4039
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Official URL: http://www.sciencedirect.com/science/article/pii/S...
Related URL: http://dx.doi.org/10.1016/j.tetlet.2007.11.177
Abstract
A new method for the stereoselective synthesis of trans-2,6-disubstituted 3,6-dihydro-2H-pyrans with a variety of substitution patterns is described, involving Lewis acid induced tandem allylation or cyanation of δ-hydroxy-α,β-unsaturated aldehydes to produce dihydropyrans in good yields and with trans-selectivity. This method is very useful for the synthesis of trans-2,6-disubstituted dihydropyran ring-containing natural products such as laulimalide, scytophycin C and many others.
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to Elsevier Science. |
| Keywords: | Dihydropyrans; δ-hydroxy-α,β-unsaturated Aldehydes; Allylation; Cyanation |
| ID Code: | 58820 |
| Deposited On: | 02 Sep 2011 03:29 |
| Last Modified: | 02 Sep 2011 03:29 |
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