Please use this identifier to cite or link to this item: 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
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