The alkaloids. Volume 86 /

Detalles Bibliográficos
Clasificación:Libro Electrónico
Otros Autores: Kn�olker, Hans-Joachim (Editor )
Formato: Electrónico eBook
Idioma:Inglés
Publicado: Cambridge, MA : Academic Press is an imprint of Elsevier, 2021.
Temas:
Alkaloids.
Alkaloids
Alcalo�ides.
Acceso en línea:Texto completo
Tabla de Contenidos:
  • Intro
  • The Alkaloids
  • Copyright
  • Contents
  • Contributors
  • Preface
  • Chapter One: Aspidosperma and Strychnos alkaloids: Chemistry and biology
  • 1. Introduction and scope
  • 2. Biological activity
  • 3. Biosynthesis of Aspidosperma and Strychnos alkaloids
  • 4. Synthesis of Aspidosperma alkaloids
  • 4.1. Rawal�s synthesis of (+)-tabersonine (ent-21), (+)-16-methoxytabersonine (ent-22) and (+)-aspidospermidine (3)
  • 4.2. Fukuyama�s synthesis of (�)-vincadifformine (26) and (-)-tabersonine (21)
  • 4.3. Murphy�s synthesis of (�)-aspidospermidine (3) and formal synthesis of (�)-vindoline (30)
  • 4.4. Heathcock�s synthesis of (�)-aspidospermidine (3)
  • 4.5. Au�b�s synthesis of (+)-aspidospermidine (3)
  • 4.6. Marino�s synthesis of (+)-aspidospermidine (3)
  • 4.7. Shishido�s synthesis of (-)-aspidospermine (8)
  • 4.8. Gnecco�s synthesis of (+)-aspidospermidine (3)
  • 4.9. Banwell�s synthesis of (�)-aspidospermidine (3) and (�)-limaspermidine (17)
  • 4.10. Boger�s synthesis of (-)-vindoline (30), (-)-vindorosine (29), spegazzinine (11), aspidospermine (8), (-)-deoxoapod ...
  • 4.11. Zard�s synthesis of (�)-aspidospermidine (3)
  • 4.12. Pearson�s formal synthesis of (�)-aspidospermidine (3) and (�)-aspidospermine (8)
  • 4.13. Coldham�s synthesis of (�)-aspidospermidine (3) and (�)-aspidospermine (8)
  • 4.14. Saito�s synthesis of (+)-aspidospermidine (3)
  • 4.15. Iwabuchi�s synthesis of (+)-aspidospermidine (3)
  • 4.16. Tomioka�s synthesis of (-)-aspidospermidine (3)
  • 4.17. Canesi�s synthesis of (�)-aspidospermidine (3)
  • 4.18. Cho�s synthesis of (�)-aspidospermidine (3), (+)-aspidospermidine (3) and (-)-tabersonine (21)
  • 4.19. MacMillan�s synthesis of (+)-aspidospermidine (3), (+)-vincadifformine (ent-26) and (-)-minovincine (27)
  • 4.20. Pandey�s synthesis of (+)-vincadifformine (ent-26), (+)-ervinceine (28) and (+)-aspidospermidine (3).
  • 4.21. Waser�s synthesis of (�)-aspidospermidine (3) and (�)-jerantinine E (25)
  • 4.22. Movassaghi�s synthesis of (-)-N-methyldehydroaspidospermidine (ent-5), (-)-N-methylaspidospermidine (ent-4), (-)-as ...
  • 4.23. Gaunt�s synthesis of (�)-aspidospermidine (3)
  • 4.24. Bach�s synthesis of (�)-aspidospermidine (3)
  • 4.25. Matsuo�s synthesis of (�)-aspidospermidine (3)
  • 4.26. Shao�s synthesis of (-)-aspidospermidine (ent-3), (-)-limaspermidine (ent-17), (+)-10-oxocylindrocarpidine (20), (+ ...
  • 4.27. Prasad�s synthesis of (-)-aspidospermidine (3)
  • 4.28. Andrade�s synthesis of (-)-aspidospermidine (3), (-)-tabersonine (21), (-)-vincadifformine (26) and (-)-16-methoxyt ...
  • 4.29. Oguri�s synthesis of (�)-vincadifformine (26)
  • 4.30. Qiu�s synthesis of (�)-N-methylaspidospermidine (4)
  • 4.31. Lus formal synthesis of (�)-aspidospermidine (3)
  • 4.32. Zhu�s synthesis of (�)-1,2-dehydroaspidospermidine (15), (�)-vincadifformine (ent-26) and (�)-aspidospermidine (3)
  • 4.33. She�s synthesis of (�)-aspidospermidine (3)
  • 4.34. Fan�s synthesis of (+)-limaspermidine (17)
  • 4.35. Nishida�s synthesis of (-)-minovincine (27)
  • 4.36. Dixon�s synthesis of (�)-vincadifformine (26)
  • 4.37. Jiang�s synthesis of (+)-aspidospermidine (3), (-)-pyrifolidine (12), (+)-vincadifformine (26) and other Aspidosper ...
  • 4.38. Zhang�s synthesis of (-)-vindorosine (29)
  • 4.39. Stoltz�s synthesis of (+)-limaspermidine (17)
  • 4.40. Liu�s formal synthesis of (�)-vindorosine (29)
  • 4.41. Moses�s semisyntheses of (-)-jerantinine A (23) and (-)-jerantinine E (25)
  • 4.42. Uluda
  • 5. Synthesis of Strychnos alkaloids
  • 5.1. Vanderwal�s synthesis of (�)-norfluorocurarine (41), (�)-strychnine (36), (�)-akuammicine (40), (�)-alstolucine B (4 ...
  • 5.2. Andrade�s synthesis of (�)-strychnine (36), (�)-akuammicine (40), (-)-akuammicine (40), (-)-norfluorocurarine (41), ...
  • 5.3. Reissig�s formal synthesis of (�)-strychnine (36)
  • 5.4. MacMillan�s synthesis of (-)-strychnine (36) and (-)-akuammicine (40)
  • 5.5. Chen�s synthesis of (�)-strychnine (36) and (�)-akuammicine (40)
  • 5.6. Tang�s synthesis of (�)-akuammicine (40) and (�)-strychnine (36)
  • 5.7. Qin�s synthesis of (+)-strychnine (ent-36)
  • 5.8. Snaddon�s synthesis of (-)-strychnine (36) and (-)-akuammicine (40)
  • 5.9. Ishikura�s synthesis of (�)-tubifoline (42)
  • 5.10. Takayama�s synthesis of (-)-kopsiyunnanine-I (39)
  • 5.11. Canesi�s synthesis of (-)-strychnopivotine (700)
  • 5.12. Xie�s synthesis of (-)-tubifoline (42), (-)-tubifolidine (43), (-)-dehydrotubifoline (628)
  • 6. Synthesis of bis-Strychnos and bis-Aspidosperma alkaloids
  • 6.1. Evanno and Poupon�s semisynthesis of (-)-leucoridine a (51)
  • 6.2. Andrade�s synthesis of (-)-leucoridines a (51) and C (52)
  • 6.3. Andrade�s semisyntheses of (-)-sungucine (53), (-)-isosungucine (54), and (-)-strychnogucine B (55)
  • 6.4. Andrade�s semisynthesis of (-)-melodinine K (56)
  • 7. Summary
  • Acknowledgments
  • Note added in proof
  • References
  • Chapter Two: Morphine alkaloids: History, biology, and synthesis
  • 1. Introduction
  • 2. History
  • 3. Isolation and structure
  • 4. Biosynthesis
  • 5. Total synthesis of morphine and congeners
  • 5.1. Mulzer (1996)
  • Dihydrocodeinone
  • 5.2. Parsons (1996)
  • Morphine
  • 5.3. White (1997)
  • ent-Morphine
  • 5.4. Mulzer (1997)
  • Dihydrocodeinone
  • 5.5. Ogasawara (2001)
  • Dihydrocodeinone ethylene ketal
  • 5.6. Taber (2002)
  • Morphine
  • 5.7. Trost (2002).
  • Codeine
  • Morphine
  • 5.8. Fukuyama (2006)
  • rac-Morphine
  • 5.9. Parker (2006)
  • Dihydrocodeinone
  • 5.10. Hudlicky (2007)
  • ent-Codeine
  • 5.11. Iorga/Guilou (2008)
  • rac-Codeine
  • 5.12. Chida (2008)
  • Dihydroisocodeine
  • 5.13. Hudlicky (2009)
  • Codeine
  • 5.14. Magnus (2009)
  • rac-Codeine
  • 5.15. Stork (2009)
  • rac-Codeine
  • 5.16. Fukuyama (2010)
  • Morphine
  • 5.17. Hudlicky (2011)
  • ent-Codeinone
  • 5.18. Metz (2011)
  • rac-Codeine
  • 5.19. Fan (2013)
  • rac-Morphine
  • 5.20. Hudlicky (2013)
  • Dihydrocodeine
  • 5.21. Hudlicky (2014)
  • ent-Hydromorphone
  • 5.22. Opatz (2014)
  • Dihydrocodeine
  • 5.23. Gaunt (2014)
  • Morphine
  • 5.24. Zhang (2015)
  • rac-Codeine
  • 5.25. Hudlicky (2016)
  • Hydromorphone
  • 5.26. Smith (2016)
  • Racemic morphine
  • 5.27. Fukuyama (2017)
  • Morphine
  • 5.28. Metz (2018)
  • Codeine
  • 5.29. Wang (2019)
  • Morphine
  • 5.30. Barriault (2019)
  • rac-Morphine
  • 6. Synthesis of medicinal derivatives
  • 6.1. Oxycodone
  • 6.1.1. Fukuyama (2014)
  • 6.1.2. Chen (2018)
  • 6.1.3. Opatz (2019)
  • 6.1.4. Hudlicky (2019)
  • 6.1.5. Industrial scale synthesis of oxycodone
  • 6.2. 10-Keto oxycodone
  • 6.2.1. Hudlicky (2019)
  • 6.3. Oxymorphone
  • 6.3.1. Rice (1978, 1998)
  • 6.3.2. Industrial scale synthesis of oxymorphone
  • 6.4. Buprenorphine
  • 6.4.1. Bentley (1961)
  • 6.4.2. Hudlicky (2011)
  • 6.4.3. Hudlicky (2012)
  • 6.5. N- and O-Dealkylation of opiates and derivatives
  • 6.5.1. N-Demethylation
  • 6.5.2. Electrophilic reagents
  • 6.5.3. Dialkyl azodicarboxylates
  • 6.5.4. Polonovski-type reactions
  • 6.5.5. Pd-catalysts
  • 6.5.6. O-Demethylation
  • 6.5.7. Br�nsted acids
  • 6.5.8. Lewis acids
  • 6.5.9. Nucleophilic O-demethylation
  • 6.5.10. Combinatorial acid and nucleophilic O-demethylation
  • 6.6. Naltrexone, methyl naltrexone and naloxone syntheses
  • 6.6.1. Industrial preparation of naloxone.
  • 6.6.2. Rice (1977 and 2015)
  • 6.6.3. Hudlicky (2012 and 2013)
  • 6.6.4. Ellman (2019)
  • 6.6.5. N-Methylnaltrexone
  • 6.6.6. Industrial synthesis of N-methylnaltrexone
  • 6.6.7. Hudlicky (2015)
  • 6.7. New horizons: Novel synthetic opioid agonists/antagonists
  • 6.7.1. Benzylidene-substituted opiates
  • 6.7.2. Portoghese (1991)
  • 6.7.3. Nagase (2012 and 2015)
  • 6.7.4. Cunningham (2017)
  • 6.7.5. MOP/NOR receptor agonists
  • 6.7.6. Ko, Husbands, and Toll (2011 and 2018)
  • 6.7.7. N-phenethyl species
  • 6.7.8. Rice (2000s-2020)
  • 7. Conclusions and outlook
  • Acknowledgments
  • Note added in Proof
  • References
  • Appendix A
  • Cumulative Index of Titles
  • Index.

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