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https://doi.org/10.1016/j.tet.2011.03.063
| Title: | A pattern recognition approach to 14-epi-hydrophenanthrene core of the morphine alkaloids based on shikimic acid | Authors: | Dinh, T.N. Chen, A. Chai, C.L.L. |
Keywords: | Hydrophenanthrene Intramolecular Heck coupling Intramolecular McMurry coupling Pattern recognition Shikimic acid |
Issue Date: | 13-May-2011 | Citation: | Dinh, T.N., Chen, A., Chai, C.L.L. (2011-05-13). A pattern recognition approach to 14-epi-hydrophenanthrene core of the morphine alkaloids based on shikimic acid. Tetrahedron 67 (19) : 3363-3368. ScholarBank@NUS Repository. https://doi.org/10.1016/j.tet.2011.03.063 | Abstract: | An expeditious and stereoselective construction of C-14-epimer of the tetracyclic hydrophenanthrene framework of the morphine alkaloids is described. The core structure is obtained in nine steps in 11% overall yield from shikimic acid via three key transformations: (i) coupling of shikimic acid with 2-iodoisovanillin at C-3 by double SN2 inversion to form the aryl ether 5; (ii) an intramolecular Heck reaction to construct the dihydrobenzofuran ring and (iii) a McMurry coupling to furnish the hydrophenanthrene core. © 2011 Published by Elsevier Ltd. | Source Title: | Tetrahedron | URI: | http://scholarbank.nus.edu.sg/handle/10635/105581 | ISSN: | 00404020 | DOI: | 10.1016/j.tet.2011.03.063 |
| Appears in Collections: | Staff Publications |
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