Mohapatra, Debendra K. ; Das, Pragna P. ; Pattanayak, Manas Ranjan ; Yadav, J. S. (2010) Iodine-catalyzed highly diastereoselective synthesis of trans-2,6-disubstituted-3,4-dihydropyrans: application to concise construction of C28-C37 bicyclic core of (+)-sorangicin A Chemistry - A European Journal, 16 (7). pp. 2072-2078. ISSN 0947-6539
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Official URL: http://onlinelibrary.wiley.com/doi/10.1002/chem.20...
Related URL: http://dx.doi.org/10.1002/chem.200902999
Abstract
A novel iodine-catalyzed highly diastereoselective synthesis of trans-2,6-disubstituted-3,4-dihydropyrans have been achieved from δ-hydroxy α,β-unsaturated aldehydes by treating with allyltrimethyl silane in THF at room temperature with good to excellent yields. This methodology has been successfully implemented for a concise asymmetric synthesis of C28-C37 dioxabicyclo[3.2.1]octane ring system of (+)-sorangicin A in 8 steps with 21 % overall yield.
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to John Wiley and Sons. |
| Keywords: | Asymmetric Synthesis; Iodine; Oxygen Heterocycles; Sorangicin A |
| ID Code: | 63123 |
| Deposited On: | 28 Sep 2011 03:48 |
| Last Modified: | 28 Sep 2011 03:48 |
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