Skip to main content
Top
Published in:
Cover of the book

2011 | OriginalPaper | Chapter

Recent Advances in the Synthesis of Morphine and Related Alkaloids

Author : Noritaka Chida

Published in: Chemistry of Opioids

Publisher: Springer Berlin Heidelberg

Activate our intelligent search to find suitable subject content or patents.

search-config
loading …

Abstract

Morphine, an alkaloid isolated from the opium poppy, has been widely used as an analgesic, and has been a fascinating synthetic target of organic chemists. After the first total synthesis reported in 1952, a number of synthetic studies toward morphine have been reported, and findings obtained in such studies have greatly contributed to the progress of synthetic organic chemistry as well as medicinal chemistry. This review provides an overview of recent studies toward the total synthesis of morphine and related alkaloids. Work reported in the literature since 2004 will be reviewed.

Graphical Abstract

Dont have a licence yet? Then find out more about our products and how to get one now:

Springer Professional "Wirtschaft+Technik"

Online-Abonnement

Mit Springer Professional "Wirtschaft+Technik" erhalten Sie Zugriff auf:

  • über 102.000 Bücher
  • über 537 Zeitschriften

aus folgenden Fachgebieten:

  • Automobil + Motoren
  • Bauwesen + Immobilien
  • Business IT + Informatik
  • Elektrotechnik + Elektronik
  • Energie + Nachhaltigkeit
  • Finance + Banking
  • Management + Führung
  • Marketing + Vertrieb
  • Maschinenbau + Werkstoffe
  • Versicherung + Risiko

Jetzt Wissensvorsprung sichern!

Springer Professional "Technik"

Online-Abonnement

Mit Springer Professional "Technik" erhalten Sie Zugriff auf:

  • über 67.000 Bücher
  • über 390 Zeitschriften

aus folgenden Fachgebieten:

  • Automobil + Motoren
  • Bauwesen + Immobilien
  • Business IT + Informatik
  • Elektrotechnik + Elektronik
  • Energie + Nachhaltigkeit
  • Maschinenbau + Werkstoffe




 

Jetzt Wissensvorsprung sichern!

Literature
1.
go back to reference Booth M (1998) Opium: a history. St. Martin’s Press, New York Booth M (1998) Opium: a history. St. Martin’s Press, New York
2.
go back to reference Kapoor LD (1995) Opium poppy: botany, chemistry, and pharmacology. The Haworth, New York Kapoor LD (1995) Opium poppy: botany, chemistry, and pharmacology. The Haworth, New York
3.
go back to reference Cordell GA (1981) Introduction to alkaloids: a biogenetic approach. Wiley, New York Cordell GA (1981) Introduction to alkaloids: a biogenetic approach. Wiley, New York
4.
go back to reference Butora G, Hudlicky T (1998) The story of morphine structure elucidation: one hundred years of deductive reasoning. In: Hudlicky T (ed) Organic synthesis: theory and applications. JAI Press, Stamford, p 1 Butora G, Hudlicky T (1998) The story of morphine structure elucidation: one hundred years of deductive reasoning. In: Hudlicky T (ed) Organic synthesis: theory and applications. JAI Press, Stamford, p 1
7.
go back to reference Maier M (1995) Synthesis of morphine. In: Waldmann H (ed) Organic synthesis highlights II. VCH, Weinheim, p 357CrossRef Maier M (1995) Synthesis of morphine. In: Waldmann H (ed) Organic synthesis highlights II. VCH, Weinheim, p 357CrossRef
8.
go back to reference Kametani T (1977) The total syntheses of isoquinoline alkaloids. In: ApSimon J (ed) The total synthesis of natural products, vol 3. Wiley, New York, p 1 Kametani T (1977) The total syntheses of isoquinoline alkaloids. In: ApSimon J (ed) The total synthesis of natural products, vol 3. Wiley, New York, p 1
9.
go back to reference Corey EJ, Cheng XM (1989) The logic of chemical synthesis. Wiley, New York Corey EJ, Cheng XM (1989) The logic of chemical synthesis. Wiley, New York
10.
go back to reference Novak BH, Hudlicky T, Reed JW, Multzer J, Trauner D (2000) Curr Org Chem 4:343CrossRef Novak BH, Hudlicky T, Reed JW, Multzer J, Trauner D (2000) Curr Org Chem 4:343CrossRef
11.
go back to reference Blakemore PR, White JD (2002) Chem Commun 1159 Blakemore PR, White JD (2002) Chem Commun 1159
12.
go back to reference Hudlicky T, Butora G, Feamley SP, Gum AG, Stabile MR (1996) A historical perspective of morphine synthesis. In: Atta-ur-Rahman (ed) Natural products chemistry, vol 18. Elsevier, Amsterdam, p 45 Hudlicky T, Butora G, Feamley SP, Gum AG, Stabile MR (1996) A historical perspective of morphine synthesis. In: Atta-ur-Rahman (ed) Natural products chemistry, vol 18. Elsevier, Amsterdam, p 45
13.
14.
go back to reference Taber DF, Neubert TD, Schlecht MF (2004) The enantioselective synthesis of morphine. In: Harmata M (ed) Strategies and tactics in organic synthesis, vol 5. Elsevier, London, p 353CrossRef Taber DF, Neubert TD, Schlecht MF (2004) The enantioselective synthesis of morphine. In: Harmata M (ed) Strategies and tactics in organic synthesis, vol 5. Elsevier, London, p 353CrossRef
16.
17.
18.
go back to reference Tsuji J (1995) Palladium reagents and catalysis. Wiley, New York Tsuji J (1995) Palladium reagents and catalysis. Wiley, New York
20.
go back to reference Hughes DL (1992) The Mitsunobu reaction. In: Paquette LE (ed) Organic reactions, vol 42. Wiley, New York, p 335 Hughes DL (1992) The Mitsunobu reaction. In: Paquette LE (ed) Organic reactions, vol 42. Wiley, New York, p 335
23.
24.
go back to reference Hsin, LW, Chang LT, Liou HL (2008) Synlett 2299 Hsin, LW, Chang LT, Liou HL (2008) Synlett 2299
25.
go back to reference Omori AT, Finn KL, Leisch H, Carroll RJ, Hudlicky T (2007) Synlett 2859 Omori AT, Finn KL, Leisch H, Carroll RJ, Hudlicky T (2007) Synlett 2859
26.
go back to reference Itoh Y, Hirao T, Saegusa T (1978) J Org Chem 43:1101 Itoh Y, Hirao T, Saegusa T (1978) J Org Chem 43:1101
27.
go back to reference Barton DHR, Motherwell RSH, Motherwell WB (1981) J Chem Soc Perkin Trans 1:2363CrossRef Barton DHR, Motherwell RSH, Motherwell WB (1981) J Chem Soc Perkin Trans 1:2363CrossRef
34.
go back to reference Johnson WS, Werthermann L, Barlett WR, Brocksom TJ, Li TT, Faulkner DJ, Petersen MR (1970) J Am Chem Soc 92:741CrossRef Johnson WS, Werthermann L, Barlett WR, Brocksom TJ, Li TT, Faulkner DJ, Petersen MR (1970) J Am Chem Soc 92:741CrossRef
35.
36.
38.
39.
go back to reference Multzer J, Bats JW, List B, Opatz T, Trauner D (1997) Synlett 441 Multzer J, Bats JW, List B, Opatz T, Trauner D (1997) Synlett 441
40.
42.
go back to reference Nagata H, Miyazawa N, Ogasawara K (2001) Chem Commun 1094 Nagata H, Miyazawa N, Ogasawara K (2001) Chem Commun 1094
43.
go back to reference Olofson RA, Martz JT, Senet JP, Piteau M, Malfroot T (1984) J Org Chem 49:2081CrossRef Olofson RA, Martz JT, Senet JP, Piteau M, Malfroot T (1984) J Org Chem 49:2081CrossRef
45.
go back to reference Stork G, Yamashita A, Damu J, Schulte GR, Chesworth R, Miyazaki Y, Farmer JJ (2009) J Am Chem Soc 131:11402CrossRef Stork G, Yamashita A, Damu J, Schulte GR, Chesworth R, Miyazaki Y, Farmer JJ (2009) J Am Chem Soc 131:11402CrossRef
47.
50.
52.
57.
go back to reference Uenishi J, Kawahama R, Shiga Y, Yonemitus O, Tsuji J (1996) Tetrahedron Lett 37:6759CrossRef Uenishi J, Kawahama R, Shiga Y, Yonemitus O, Tsuji J (1996) Tetrahedron Lett 37:6759CrossRef
60.
go back to reference Kawasaki M, Suzuki Y, Terashima S (1985) Chem Pharm Bull 33:52 Kawasaki M, Suzuki Y, Terashima S (1985) Chem Pharm Bull 33:52
62.
go back to reference Corey EJ, Bakshi RK, Shibata S, Chen CP, Singh VK (1987) J Am Chem Soc 109:7925CrossRef Corey EJ, Bakshi RK, Shibata S, Chen CP, Singh VK (1987) J Am Chem Soc 109:7925CrossRef
65.
go back to reference Omori AT, Finn KJ, Leisch H, Carroll RJ, Hudlicky T (2007) Synlett 2859 Omori AT, Finn KJ, Leisch H, Carroll RJ, Hudlicky T (2007) Synlett 2859
66.
go back to reference Leisch H, Omori AT, Finn KJ, Gilmet J, Bissett T, Ilceski D, Hudlicky T (2009) Tetrahedron 65:9862CrossRef Leisch H, Omori AT, Finn KJ, Gilmet J, Bissett T, Ilceski D, Hudlicky T (2009) Tetrahedron 65:9862CrossRef
67.
71.
Metadata
Title
Recent Advances in the Synthesis of Morphine and Related Alkaloids
Author
Noritaka Chida
Copyright Year
2011
Publisher
Springer Berlin Heidelberg
DOI
https://doi.org/10.1007/128_2010_73