Expeditious divergent synthetic approach to polycyclic terpene-like molecules

Chemistry - A European Journal

Volumn 17, Issue 7, 2011, Pages 2048-2051

  Boddaert, Thomas ^a   Coquerel, Yoann ^a   Rodriguez, Jean ^a  

^a CNRS   (France)

Author keywords

consecutive reactions; domino reactions; natural products; one pot reactions; terpenoids

Indexed keywords

CONDENSATION REACTIONS; KETONES; REACTION KINETICS;

CONSECUTIVE REACTION; DOMINO REACTIONS; NATURAL PRODUCTS; ONE-POT REACTION; TERPENOIDS;

TERPENES;

EID: 79551694037     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201003261     Document Type: Article

References (52)

1. G. M. Cragg, P. G. Grothaus, D. J. Newman, Chem. Rev. 2009, 109, 3012-3043
2. D. J. Newman, G. M. Cragg, J. Nat. Prod. 2007, 70, 461-477.
3. R. M. Wilson, S. J. Danishefsky, J. Org. Chem. 2006, 71, 8329-8351
4. C. Cordier, D. Morton, S. Murrison, A. Nelson, C. O'Leary-Steele, Nat. Prod. Rep. 2008, 25, 719-737
5. P. A. Wender, V. A. Verma, T. J. Paxton, T. H. Pillow, Acc. Chem. Res. 2008, 41, 40-49
6. K. Kumar, H. Waldmann, Angew. Chem. 2009, 121, 3272-3290
7. Angew. Chem. Int. Ed. 2009, 48, 3224-3242.
8. For efforts to clarify the terminologies of MBFTs, see
9. L. F. Tietze, U. Beifuss, Angew. Chem. 1993, 105, 137-170
10. Angew. Chem. Int. Ed. Engl. 1993, 32, 131-163
11. L. F. Tietze, Chem. Rev. 1996, 96, 115-136
12. Domino Reactions in Organic Synthesis (Eds.:, L.F. Tietze, G. Brasche, K.M. Gericke,), Wiley-VCH, Weinheim, 2006
13. Y. Coquerel, T. Boddaert, M. Presset, D. Mailhol, J. Rodriguez, in Ideas in Chemistry and Molecular Sciences: Advances in Synthetic Chemistry (Ed.:, B. Pignataro,), Wiley-VCH, Weinheim, 2010, Chaptera 9, pp. 187-202.
14. Recent reviews
15. K. C. Nicolaou, J. S. Chen, Chem. Soc. Rev. 2009, 38, 2993-3009
16. B. B. Touré, D. G. Hall, Chem. Rev. 2009, 109, 4439-4486
17. C. Grondal, M. Jeanty, D. Enders, Nat. Chem. 2010, 2, 167-178.
18. 1,6]dodecane compounds: for 1 and related compounds, see
19. M. Presset, Y. Coquerel, J. Rodriguez, Eur. J. Org. Chem. 2010, 2247-2260; for 2 and related compounds, see
20. J.-M. Gao, W.-J. Wu, J.-W. Zhang, Y. Konishi, Nat. Prod. Rep. 2007, 24, 1153-1189; for 3-5 and related compounds, see
21. H.-D. Sun, S.-X. Huang, Q.-B. Han, Nat. Prod. Rep. 2006, 23, 673-698.
22. 1,6]dodecane will be used throughout the manuscript.
23. For previous preparation of analogues of 7 in two steps, see:, T. Boddaert, Y. Coquerel, J. Rodriguez, Adv. Synth. Catal. 2009, 351, 1744-1748; erratum
24. T. Boddaert, Y. Coquerel, J. Rodriguez, Adv. Synth. Catal. 2009, 351, 2541.
25. 2 was equally efficient, although slower than in toluene:, M. Presset, Y. Coquerel, J. Rodriguez, J. Org. Chem. 2009, 74, 415-418.
26. For reviews, see
27. Y. Coquerel, J. Rodriguez, Eur. J. Org. Chem. 2008, 1125-1132
28. F. Nicks, Y. Borguet, S. Delfosse, D. Bicchielli, L. Delaude, X. Sauvage, A. Demonceau, Aust. J. Chem. 2009, 62, 184-207; for related CM reactions, see
29. A. Michaut, T. Boddaert, Y. Coquerel, J. Rodriguez, Synthesis 2007, 2867-2871
30. T. Boddaert, Y. Coquerel, J. Rodriguez, C. R. Chim. 2009, 12, 872-875; for discussion, see
31. D. Dallinger, M. Irfan, A. Suljanovic, C. O. Kappe, J. Org. Chem. 2010, 75, 5278-5288.
32. S. Fustero, D. Jiménez, M. Sánchez-Roselló, C. delaPozo, J. Am. Chem. Soc. 2007, 129, 6700-6701
33. J.-R. Chen, C.-F. Li, X.-L. An, J.-J. Zhang, X.-Y. Zhu, W.-J. Xiao, Angew. Chem. 2008, 120, 2523-2526
34. Angew. Chem. Int. Ed. 2008, 47, 2489-2492
35. H. Fuwa, K. Noto, M. Sasaki, Org. Lett. 2010, 12, 1636-1639.
36. M.-H. Filippini, R. Faure, J. Rodriguez, J. Org. Chem. 1995, 60, 6872-6882
37. M.-H. Filippini, J. Rodriguez, Chem. Rev. 1999, 99, 27-76.
38. J. D. More, N. S. Finney, Org. Lett. 2002, 4, 3001-3003.
39. 2O), 794647 (6 c) and 794648 (6 e) contain the supplementary crystallographic data for thie paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via.
40. E. Vedrenne, H. Dupont, S. Oualef, L. Elkaïm, L. Grimaud, Synlett 2005, 670-672. For a review on olefin metathesis reactions in the presence of a basic amine, see
41. P. Compain, Adv. Synth. Catal. 2007, 349, 1829-1846.
42. A. K. Banerjee, M. S. Laya Mimó, W. J. Vera Vegas, Rus. Chem. Rev. 2001, 70, 971-990.
43. The aldolization may however be reversible under the reaction conditions.
44. Y. Asakawa, M. Toyota, T. Takemoto, Tetrahedron Lett. 1978, 19, 1553-1556
45. Y. Asakawa, M. Toyota, T. Takemoto, I. Kubo, K. Nakanishi, Phytochemistry 1980, 19, 2147-2154.
46. Y.-B. Cheng, J.-Y. Jang, A. T. Khalil, Y.-H. Kuo, Y.-C. Shen, J. Nat. Prod. 2006, 69, 675-678.
47. Y. Coquerel, D. Bensa, V. Moret, J. Rodriguez, Synlett 2006, 2751-2754 (erratum
48. Y. Coquerel, D. Bensa, V. Moret, J. Rodriguez, Synlett 2006, 3368)
49. Y. Coquerel, D. Bensa, A. Doutheau, J. Rodriguez, Org. Lett. 2006, 8, 4819-4822
50. Y. Coquerel, M.-H. Filippini, D. Bensa, J. Rodriguez, Chem. Eur. J. 2008, 14, 3078-3092
51. I. Reboul, T. Boddaert, Y. Coquerel, J. Rodriguez, Eur. J. Org. Chem. 2008, 5379-5382.
52. The trans-lactonization possibly proceeded through initial opening of the fused lactone with methanol, particularly in the case of 17 b.