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Please use this identifier to cite or link to this item: https://doi.org/10.1016/j.tet.2011.03.063
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dc.titleA pattern recognition approach to 14-epi-hydrophenanthrene core of the morphine alkaloids based on shikimic acid
dc.contributor.authorDinh, T.N.
dc.contributor.authorChen, A.
dc.contributor.authorChai, C.L.L.
dc.date.accessioned2014-10-29T01:47:43Z
dc.date.available2014-10-29T01:47:43Z
dc.date.issued2011-05-13
dc.identifier.citationDinh, 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
dc.identifier.issn00404020
dc.identifier.urihttp://scholarbank.nus.edu.sg/handle/10635/105581
dc.description.abstractAn 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.
dc.description.urihttp://libproxy1.nus.edu.sg/login?url=http://dx.doi.org/10.1016/j.tet.2011.03.063
dc.sourceScopus
dc.subjectHydrophenanthrene
dc.subjectIntramolecular Heck coupling
dc.subjectIntramolecular McMurry coupling
dc.subjectPattern recognition
dc.subjectShikimic acid
dc.typeArticle
dc.contributor.departmentPHARMACY
dc.description.doi10.1016/j.tet.2011.03.063
dc.description.sourcetitleTetrahedron
dc.description.volume67
dc.description.issue19
dc.description.page3363-3368
dc.description.codenTETRA
dc.identifier.isiut000290602000009
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