Crossref journal-article
Wiley
Chemistry – A European Journal (311)
Abstract

AbstractThe evolution of a total synthesis of the exiguamines, two structurally unusual natural products that are highly active inhibitors of indolamine‐2,3‐dioxygenase (IDO), is described. The ultimately successful strategy involves advanced cross‐coupling methodology and features a potentially biosynthetic tautomerization/electrocyclization cascade reaction that forms two heterocycles and installs a quaternary ammonium ion in a single synthetic operation.

Bibliography

Sofiyev, V., Lumb, J., Volgraf, M., & Trauner, D. (2012). Total Synthesis of Exiguamines A and B Inspired by Catecholamine Chemistry. Chemistry – A European Journal, 18(16), 4999–5005. Portico.

Authors 4
  1. Vladimir Sofiyev (first)
  2. Jean‐Philip Lumb (additional)
  3. Matthew Volgraf (additional)
  4. Dirk Trauner (additional)
References 48 Referenced 35
  1. 10.1007/s00018-007-7140-9
  2. {'key': 'e_1_2_6_3_2', 'first-page': '938', 'volume': '10', 'author': 'Liu X.', 'year': '2010', 'journal-title': 'Curr. Cancer Drug Targets'} / Curr. Cancer Drug Targets by Liu X. (2010)
  3. 10.1038/nrc2639
  4. 10.1073/pnas.0508996103
  5. 10.1038/nm1196
  6. 10.1021/ol900972j
  7. 10.1021/np060111x
  8. 10.1021/ja067211
  9. 10.1021/jm800143h
  10. 10.1038/nchembio.107
  11. 10.1021/ol052472u
  12. 10.1021/jo00058a056
  13. 10.1039/b006860h
  14. 10.1038/sj.bjp.0706416
  15. 10.1021/jo701402b
  16. 10.1021/jo9815397
  17. 10.1002/hlca.19880710412
  18. 10.1021/jo00116a049
  19. 10.1021/jm00264a011
  20. 10.1016/S0040-4039(00)84424-X
  21. V. Sofiyev “Synthetic studies of the Thio‐Nazarov Cyclization. Biomimetic Total Syntheses of Shimalactones and Exiguamines. Synthesis of Photoswitchable Dopamine Analogs” Ph.D. dissertation University or California Berkeley 2010.
  22. 10.1080/00397919108020836
  23. 10.1021/jm000339w
  24. 10.1139/v62-084
  25. 10.1016/S0040-4039(01)00258-1
  26. 10.1021/ja991500z
  27. 10.1021/cr60270a005
  28. 10.3987/COM-96-7722
  29. 10.1039/a909834h
  30. 10.1248/cpb.44.55
  31. 10.1126/science.1204183
  32. 10.1021/jo9823339
  33. 10.1021/jo00167a014
  34. 10.1021/ol8009013
  35. 10.1016/S0040-4020(01)90360-6
  36. 10.1021/jo035165f
  37. 10.1016/S0040-4020(98)01100-4
  38. 10.1021/ja01151a030
  39. 10.1063/1.464913
  40. 10.1139/p80-159
  41. 10.1021/j100096a001
  42. Jaguar version 6.5 Schrödinger LLC New York NY 2006.
Dates
Type When
Created 13 years, 5 months ago (March 13, 2012, 11:46 a.m.)
Deposited 1 year, 11 months ago (Aug. 30, 2023, 2:47 p.m.)
Indexed 5 days, 12 hours ago (Aug. 23, 2025, 1:07 a.m.)
Issued 13 years, 5 months ago (March 13, 2012)
Published 13 years, 5 months ago (March 13, 2012)
Published Online 13 years, 5 months ago (March 13, 2012)
Published Print 13 years, 4 months ago (April 16, 2012)
Funders 0

None

@article{Sofiyev_2012, title={Total Synthesis of Exiguamines A and B Inspired by Catecholamine Chemistry}, volume={18}, ISSN={1521-3765}, url={http://dx.doi.org/10.1002/chem.201103605}, DOI={10.1002/chem.201103605}, number={16}, journal={Chemistry – A European Journal}, publisher={Wiley}, author={Sofiyev, Vladimir and Lumb, Jean‐Philip and Volgraf, Matthew and Trauner, Dirk}, year={2012}, month=mar, pages={4999–5005} }