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

Wikimedia Foundation. 2010.

Игры ⚽ Нужно решить контрольную?

Look at other dictionaries:

  • Galanthamine total synthesis — ; 2006; 106(1) pp 116 133; (Review) DOI|10.1021/cr040415t] The natural source of galantamine are certain species of daffodil and because these species are scarce and because the isolation of galanthamine from daffodil is expensive (a 1996 figure… …   Wikipedia

  • Morphine — This article is about the drug. For other meanings, see Morphine (disambiguation). Morphia redirects here. For other uses, see Morphia (disambiguation). Not to be confused with Morphinae, Morphea, or Morpholine. Morphine …   Wikipedia

  • morphine — morphinic /mawr fin ik/, adj. /mawr feen/, n. Pharm. a white, bitter, crystalline alkaloid, C17H19NO3·H2O, the most important narcotic and addictive principle of opium, obtained by extraction and crystallization and used chiefly in medicine as a… …   Universalium

  • Marshall D. Gates, Jr. — Marshall D. Gates, Jr. Born 1915 Died 2003 Nationality American …   Wikipedia

  • Ibogaine — drugbox IUPAC name = 12 Methoxyibogamine width = 180 CAS number = 83 74 9 PubChem = 363272 C=20 | H=26 | N=2 | O=1 molecular weight = 310.433 g/mol smiles = CCC1CC2CC3C1N(C2)CCC4=C3NC5=C4C=C(C=C5)OC melting point = 152 melting high = 153… …   Wikipedia

  • Natural product — Paclitaxel (Taxol) is a natural product derived from the Yew tree.[1] A natural product is a chemical compound or substance produced by a living organism found in nature that usually has a pharmacological or biological activity for use in… …   Wikipedia

  • Trost asymmetric allylic alkylation — The Trost asymmetric allylic alkylation or Trost AAA or allylic asymmetric substitution is an organic reaction used in asymmetric synthesis. [Trost, B. M.; Fullerton, T. J. New synthetic reactions. Allylic alkylation. J. Am. Chem. Soc. 1973, 95 …   Wikipedia

  • Scopolamine — Systematic (IUPAC) name (–) (S) 3 hydroxy 2 pheny …   Wikipedia

  • Trost asymmetrische allylische Alkylierung — Die Trostsche asymmetrische allylische Alkylierung, oder einfach Asymmetrische allylische Alkylierung (AAA), ist eine Namensreaktion aus dem Bereich der Organischen Chemie. Sie dient meist der Einführung von Alkoholen, Aminen oder Derivaten von… …   Deutsch Wikipedia

  • Trostsche asymmetrische allylische Alkylierung — Die Trostsche asymmetrische allylische Alkylierung, oder einfach Asymmetrische allylische Alkylierung (AAA), ist eine Namensreaktion aus dem Bereich der Organischen Chemie. Sie dient meist der Einführung von Alkoholen, Aminen oder Derivaten von… …   Deutsch Wikipedia

Share the article and excerpts

Direct link
Do a right-click on the link above
and select “Copy Link”