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A pattern recognition approach to 14-epi-hydrophenanthrene core of the morphine alkaloids based on shikimic acid |
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| Authors: | Tung N DinhAnqi Chen Christina LL Chai |
| Institution: | a Institute of Chemical and Engineering Sciences (ICES), Agency for Science, Technology and Research (A∗STAR), n8 Biomedical Grove, Neuros #07-01, Singapore 138665 b Department of Pharmacy, National University of Singapore, 18 Science Drive 4, Singapore 117543 |
| 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. |
| Keywords: | Pattern recognition Hydrophenanthrene Shikimic acid Intramolecular Heck coupling Intramolecular McMurry coupling |
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