Morphine total synthesis

Morphine total synthesis
Morphine

Morphine total synthesis in chemistry describes the total synthesis of the alkaloid morphine. The first synthesis by Marshall D. Gates, Jr. in 1952 is considered a classic in the field.[1][2]

Several other syntheses were reported, notably by the research groups of Rice,[3] Evans,[4] Fuchs,[5] Parker,[6] Overman,[7] Mulzer-Trauner,[8] White,[9] Taber,[10] Trost,[11] Fukuyama,[12] Guillou[13] and Stork.[14]

Gates Synthesis

Gates' total synthesis of morphine is one of the first example of the Diels-Alder reaction in the context of total synthesis.

Gates synthesis.png

External links

References

  1. ^ Gates, M. D.; Tschudi, G. J. Am. Chem. Soc. 1952, 74 (4), 1109–1110. doi:10.1021/ja01588a033
  2. ^ Gates, M. D.; Tschudi, G. J. Am. Chem. Soc. 1956, 78 (7), 1380–1393. doi:10.1021/ja01588a033
  3. ^ Rice, K. C. J. Org. Chem. 1980, 45 (15), 3135-3137. doi:10.1021/jo01303a045
  4. ^ Evans, D. A.; Mitch, C. H. Tetrahedron Lett., 1982, 23 (3), 285-288. doi:10.1016/S0040-4039(00)86810-0
  5. ^ Toth, J. E.; Hamann, P. R.; Fuchs, P. L. J. Org. Chem. 1988, 53 (20), 4694-4708. doi:10.1021/jo00255a008
  6. ^ Parker, K. A.; Fokas, D. J. Am. Chem. Soc., 1992, 114 (24), 9688-9689. doi:10.1021/ja00050a075
  7. ^ Hong, C. Y.; Kado, N.; Overman, L. E. J. Am. Chem. Soc., 1993, 115 (23), 11028-11029. doi:10.1021/ja00076a086
  8. ^ Mulzer, J.; Dürner, G.; Trauner, D. Angew. Chem. Int. Ed., 1996, 35 (23-24), 2830-2832. doi:10.1002/anie.199628301
  9. ^ White, J. D.; Hrnciar, P.; Stappenbeck, F. J. Org. Chem. 1999, 64 (21), 7871-7884. doi:10.1021/jo990905z
  10. ^ Taber, D. F.; Neubert, T. D.; Rheingold, A. L. J. Am. Chem. Soc., 2002, 124 (42), 12416–12417. doi:10.1021/ja027882h
  11. ^ Trost, B. M.; Tang, W. J. Am. Chem. Soc., 2002, 124 (49), 14542-14543. doi:10.1021/ja0283394
  12. ^ Uchida, K.; Yokoshima, S.; Kan, T.; Fukuyama, T. Org. Lett., 2006, 8 (23), 5311-5313. doi:10.1021/ol062112m
  13. ^ Varin, M.; Barré, E.; Iorga, B.; Guillou, C. Chem. Eur. J., 2008, 14 (22), 6606-6608. doi:10.1002/chem.200800744
  14. ^ Stork, G.; Yamashita, A.; Adams, J.; Schulte, G. R.; Chesworth, R.; Miyazaki, Y.; Farmer, J. J. J. Am. Chem. Soc., 2009, 131 (32), 11402-11406. doi:10.1021/ja9038505

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