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Current Organic Synthesis

Editor-in-Chief

ISSN (Print): 1570-1794
ISSN (Online): 1875-6271

Syntheses of Morphine and Codeine (1992 - 2002): Templates for Exploration of Synthetic Tools

Author(s): L. M. Mascavage, M. L. Wilson and D. R. Dalton

Volume 3, Issue 1, 2006

Page: [99 - 120] Pages: 22

DOI: 10.2174/157017906775473939

Price: $65

Abstract

Morphine (1) and its O-methylated analogue codeine (2), analgesic alkaloids of the opium poppy (Papaver Somniferium), have been targets of organic chemists engaged in synthetic activities for at least half a century. The "first" (Gates) and "most efficient" (Rice) syntheses of morphine (1) and codeine (2) are well known and have been reviewed and analyzed extensively numerous times. However, syntheses of the same two alkaloids that have been reported since 1992 and which have been used as devices to advance the art of organic synthesis are not as widely recognized and they have not been as thoroughly reviewed. Here they are analyzed in the spirit of the use of these two compounds as templates. Further, since both racemic and enantiospecific syntheses are important and since all eight (8) approaches (since 1992) are sufficiently different so as to warrant more tha n superficial examination, they are all considered.

Keywords: tetrahydrofuran (THF), crystal x-ray diffraction, Thebainone, osmium tetroxide dihydroxylation, lipase oxidation, DEAD, codeine


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