Manipulating Simple Reactive Chemical Units: Fishing for Alkaloids from Complex Mixtures

Chemistry - A European Journal

Volumn 21, Issue 30, 2015, Pages 10604-10615

  Poupon, Erwan ^a   Gravel, Edmond ^b  

^a CNRS   (France)

^b SERVICE DE CHIMIE BIOORGANIQUE ET DE MARQUAGE   (France)

Author keywords

alkaloids; biomimetic synthesis; lysine; myrioneuron; nitraria

Indexed keywords

ALKALOIDS; AMINO ACIDS; BIOMIMETIC PROCESSES; BIOMIMETICS; CARBON; METABOLITES; SCAFFOLDS (BIOLOGY);

BIOMIMETIC SYNTHESIS; LYSINE; MOLECULAR SCAFFOLDS; MYRIONEURON; NITRARIA; REACTIVE CHEMICALS; REACTIVE INTERMEDIATE; TETRAHYDROPYRIDINE;

MIXTURES;

EID: 84937425385     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201500366     Document Type: Article

References (51)

1. E. Gravel, in Biomimetic Organic Synthesis Vol. 1 (Eds:, E. Poupon, B. Nay,), Wiley-VCH, Weinheim, 2011, chap. 8, pp.271-315.
2. E. Poupon, R. Salame, L.-H. Yan, in Biomimetic Organic Synthesis Vol. 1 (Eds:, E. Poupon, B. Nay,), Wiley-VCH, Weinheim, 2011, chap. 1, pp.3-60. In addition to the present article, the interested reader may also refer to closely related studies on the biomimetic synthesis of ornithine-derived alkaloids such as
3. C. C. Struve, C. Christopherson, Heterocycles 2003, 60, 1907-1914; and
4. P. D. Brown, A. C. Willis, M. S. Sherburn, A. L. Lawrence, Angew. Chem. Int. Ed. 2013, 52, 13273-13275
5. Angew. Chem. 2013, 125, 13515-13517.
6. See many textbook chapters, among others:, P. Dewick, in Medicinal Natural Products, a Biosynthetic Approach, 3 rd ed., Wiley, Chichester, chap. 6, pp.311-420.
7. H.-P. Husson, J. Royer, Chem. Soc. Rev. 1999, 28, 383-394.
8. E. Gravel, E. Poupon, Nat. Prod. Rep. 2010, 27, 32-56.
9. M. J. Wanner, G.-J. Koomen, in Studies in Natural Products Chemistry: Stereoselectivity in Synthesis and Biosynthesis of Lupine and Nitraria Alkaloids Vol. 14 (Ed:, Atta-ur-Rahman,), Elsevier, Amsterdam, 1994, pp.731-768
10. M. J. Wanner, G. J. Koomen, Pure Appl. Chem. 1994, 66, 2239-2242
11. M. J. Wanner, G. J. Koomen, Pure Appl. Chem. 1996, 68, 2051-2056
12. M. J. Wanner, G. J. Koomen, J. Indian Chem. Soc. 1997, 74, 891-895.
13. E. J. Sorensen, Bioorg. Med. Chem. 2003, 11, 3225-3228.
14. H. Kessler, H. Möhrle, G. Zimmermann, J. Org. Chem. 1977, 42, 66-70.
15. E. Gravel, E. Poupon, R. Hocquemiller, Tetrahedron 2006, 62, 5248-5253.
16. C. Schöpf, F. Braun, A. Komzak, Chem. Ber. 1956, 89, 1821-2833.
17. R. Salame, E. Gravel, P. Retailleau, E. Poupon, Org. Biomol. Chem. 2010, 8, 2522-2528.
18. T. Tashima, M. Imai, Y. Kuroda, S. Yagi, T. Nakagawa, J. Org. Chem. 1991, 56, 694-697. At that time, there was no information concerning the stereochemistry of glutaraldehyde dimer 25.
19. Unpublished result; treatment of 26 with (R)-(-)-phenylglycinol resulted in the cascade formation of spiranic compound A, a direct precursor of isonitramines, see:, J.-C. Quirion, D. S. Grierson, J. Royer, H.-P. Husson, Tetrahedron Lett. 1988, 29, 3311-3314.
20. M. J. Wanner, G.-J. Koomen, J. Org. Chem. 1995, 60, 5634-5637.
21. E. Gravel, E. Poupon, R. Hocquemiller, Org. Lett. 2005, 7, 2497-2499.
22. E. Gravel, A. Harfouche, R. Salame, K. Leblanc, A. Maciuk, E. Poupon, Chem. Eur. J. 2013, 19, 14515-14520.
23. G. Gribble, J. Org. Chem. 1972, 37, 1833-1835.
24. R. Salame, E. Gravel, K. Leblanc, E. Poupon, Org. Lett. 2009, 11, 1891-1894
25. T. Putkonen, A. Tolvanen, R. Jokela, Tetrahedron Lett. 2001, 42, 6593-6594
26. T. Putkonen, A. Tolvanen, R. Jokela, S. Caccamese, N. Parinello, Tetrahedron 2003, 59, 8589-8595
27. S. Luo, C. A. Zificsak, R. P. Hsung, Org. Lett. 2003, 5, 4709-4712
28. T.-L. Ho, C.-K. Chen, Helv. Chim. Acta 2006, 89, 122-126
29. S. Luo, J. Zhao, H. Zhai, J. Org. Chem. 2004, 69, 4548-4550
30. J. A. Wilkinson, N. Ardes-Guisot, S. Ducki, J. Leonard, Tetrahedron Lett. 2005, 46, 8053-8056. For total syntheses published since 2009
31. T. Nemoto, E. Yamamoto, R. Franzén, T. Fukuyama, R. Wu, T. Fukamachi, H. Kobayashi, Y. Hamada, Org. Lett. 2010, 12, 872-875
32. S. A. M. W. vandenBroek, J. G. H. Lemmers, F. L. vanDelft, F. P. J. T. Rutjes, Org. Biomol. Chem. 2012, 10, 945-951
33. H. Flink, R. Jokela, Tetrahedron 2012, 68, 3811-3814.
34. R. Salame, E. Gravel, E. Poupon, Tetrahedron Lett. 2011, 52, 6453-6456.
35. F. Arioli, M. Pérez, F. Subrizi, N. Llor, J. Bosch, M. Amat, J. Org. Chem. 2014, 79, 7740-7745.
36. M. J. Wanner, G.-J. Koomen, J. Org. Chem. 1994, 59, 7479-7484
37. D. François, M.-C. Lallemand, M. Selkti, A. Tomas, N. Kunesch, H.-P. Husson, J. Org. Chem. 1997, 62, 8914-8916.
38. P. Champy, in Biomimetic Organic Synthesis Vol. 2 (Eds:, E. Poupon, B. Nay,), Wiley-VCH, Weinheim, 2011, chap. 24, pp. 849-934.
39. Alkaloids from Myrioneuron nutans, see
40. V. C. Pham, A. Jossang, P. Grellier, T. Sévenet, V. H. Nguyen, B. Bodo, J. Org. Chem. 2008, 73, 7565-7573, and references cited therein. For alkaloids from Myrioneuron faberi see
41. S.-D. Huang, Y. Zhang, M.-M. Cao, Y.-T. Di, G.-H. Tang, Z.-G. Peng, J.-D. Jiang, H.-P. He, X.-J. Hao, Org. Lett. 2013, 15, 590-593
42. M.-M. Cao, S.-D. Huang, Y.-T. Di, C.-M. Yuan, G.-Y. Zuo, Y.-C. Gu, Y. Zhang, X.-J. Hao, Org. Lett. 2014, 16, 528-531.
43. Unpublished results from our laboratory. For the first total synthesis of myrioneurinol, see these important papers
44. A. J. Nocket, S. M. Weinreb, Angew. Chem. Int. Ed. 2014, 53, 14162-14165
45. Angew. Chem. 2014, 126, 14386-14389
46. A. J. Nocket, Y. Feng, S. M. Weinreb, J. Org. Chem. 2015, 80, 1116-1129.
47. I. S. Young, P. S. Baran, Nat. Chem. 2009, 1, 193-205
48. T. Gaich, P. S. Baran, J. Org. Chem. 2010, 75, 4657-4673.
49. A. Skiredj, M. A. Beniddir, D. Joseph, K. Leblanc, G. Bernadat, L. Evanno, E. Poupon, Angew. Chem. Int. Ed. 2014, 53, 6419-6424
50. Angew. Chem. 2014, 126, 6537-6542
51. A. Skiredj, M. A. Beniddir, D. Joseph, K. Leblanc, G. Bernadat, L. Evanno, E. Poupon, Org. Lett. 2014, 16, 4980-4983.