Particular behavior of 'C6C2 units' in the Chichibabin pyridine synthesis and biosynthetic implications

Tetrahedron Letters

Volumn 52, Issue 27, 2011, Pages 3523-3526

  Dagorn, Flore ^a   Yan, Lok Hang ^a   Gravel, Edmond ^a,b   Leblanc, Karine ^a   MacIuk, Alexandre ^a   Poupon, Erwan ^a  

^a UNIVERSITÉ PARIS SACLAY   (France)

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

Author keywords

Alkaloids; Chichibabin pyridine synthesis; Enamine; Pyridiniums

Indexed keywords

ALKALOID DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; PYRIDINE DERIVATIVE;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; SYNTHESIS;

EID: 79957951217     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2011.05.014     Document Type: Article

References (21)

1. M.D. Hill Chem. Eur. J. 16 2010 12052 12062
2. F. Liéby-Muller, C. Allais, T. Constantieux, and J. Rodriguez Chem. Commun. 2008 4207 4209
3. C. Allais, T. Constantieux, and J. Rodriguez Chem. Eur. J. 15 2009 12945 12948
4. L. Shen, S. Cao, J. Wu, J. Zhang, H. Li, N. Liu, and X. Qian Green Chem. 11 2009 1414 1420
5. J. Liu, C. Wang, L. Wu, F. Liang, and G. Huang Synthesis 2010 4228 4234
6. Despite focusing in this paper on metal-free strategies, highly appealing syntheses are also available towards polysubstituted pyridines, see for example the exploitation of olefin cross metathesis: T.J. Donohoe, J.A. Basutto, J.F. Bower, and A. Rathi Org. Lett. 13 2011 1036 1039 and references cited therein
7. A.E. Chichibabin J. Russ. Phys. Chem. Soc. 37 1906 1229
8. B.B. Snider, and B.J. Neubert Org. Lett. 7 2005 2715 2718
9. This behavior was outlined by Baran and co-workers in a paper dedicated to the understanding of haouamines biosynthesis (Burns, N. Z.; Baran, P. S. Angew. Chem., Int. Ed. 2008, 47, 205-208). This article revealed that former results from some of us (published in 2007 in Chem. Commun.) were in fact wrong. The publication in question was immediately withdrawn on the authors' initiative. In fact intolerable thoughtlessness led to conclusions that could not be experimentally verified at that time. The present Letter is, if possible, partly rectifying and clarifying the issue with unarguable experimental data that are fully provided as supporting information to this article. The corresponding author also wishes to deeply apologize for prejudices the precedent article may have brought to the scientific community. A similar misleading conclusion also appeared in previous work: Yu, L.-B.; Chen, D.; Li, J.; Ramirez, J.; Wang, P. G. J. Org. Chem. 1997, 62, 208-211.
10. This particular behavior was also pointed out under the classical conditions of the Chichibabin pyridine synthesis, see: E.L. Eliel, R.T. McBride, and S. Kaufmann J. Am. Chem. Soc. 75 1953 4291 4296
11. Full experimental procedures, spectral characterization of compounds 11, 12, 14 and 18 are provided in Supplementary data.
12. T.-H. Chuang, Y.-C. Chen, and S. Pola J. Org. Chem. 75 2010 6625 6630
13. Under the conditions of the Chichibabin pyridine synthesis (see Ref. 9), pyridines of type B predominated whereas the obtention of the awaited 3,5,6-substituted pyridine of type A 'could not be readily duplicated' (see also Ref. 6 in Ref. 9).
14. Compound 13, m/z = 514 could not be detected in mass spectra (ESI) but a m/z = 488 was present that could correspond to dihydropyridinium 10 as a consequence of the loss of cyanide during ionization. The mass of pyridinium 12 (m/z = 396) was also detected.
15. Q. Li, A. Fan, Z. Lu, Y. Cui, W. Lin, and Y. Jia Org. Lett. 12 2010 4066 4069
16. see also: X. Wan, D. Xing, Z. Fang, B. Li, F. Zhao, K. Zhang, L. Yang, and Z. Shi J. Am. Chem. Soc. 128 2006 12046 12047
17. And: K. Papadopoulou, and J.M. Ames J. Agric. Food Chem. 42 1994 1104 1109
18. Two mechanisms for the formation of pyrroles are provided by Li et al. in Ref. 14a, only one is given in the present Letter.
19. L. Garrido, E. Zubía, M.J. Ortega, and J. Salvá J. Org. Chem. 68 2003 293 299
20. In the course of the preparation of this manuscript, Jia and co-workers disclosed the beautiful total synthesis of several lamellarins, that is, lamellarins D, H, R and ningalin B, in a paper in which the term 'biomimetic' is used to describe their oxidative pyrrole formation (see Ref. 14a), see: Li, Q.; Jiang, J.; Fan, A.; Cui, Y.; Jia, Y. Org. Lett. 2011, 13, 312-315.
21. When dealing with 2-aminopyrrrole natural products, A very interesting strategy (despite non biomimetic), relying on multicomponent reactions was recently disclosed and enabled the total synthesis of rigidins A-D: Frolova, L. V.; Evdokimov, N. M.; Hayden, K.; Malik, I.; Rogelj, S.; Kornienko, A.; Magedov, I. V. Org. Lett. 2011, 13, 1118-1121.