Total synthesis of linoxepin through a palladium-catalyzed domino reaction

Angewandte Chemie - International Edition

Volumn 52, Issue 11, 2013, Pages 3191-3194

  Tietze, Lutz F ^a   Duefert, Svenia C ^a   Clerc, Jérôme ^a   Bischoff, Matthias ^a   Maaß, Christian ^a   Stalke, Dietmar ^a  

^a UNIVERSITY OF GÖTTINGEN   (Germany)

Author keywords

domino reactions; lignans; palladium; structure elucidation; total synthesis

Indexed keywords

DOMINO REACTIONS; LIGNANS; PALLADIUM-CATALYZED; SONOGASHIRA REACTIONS; STRUCTURE ELUCIDATION; TOTAL SYNTHESIS;

CATALYSIS; PALLADIUM; REACTION KINETICS;

SYNTHESIS (CHEMICAL);

LIGNAN; LINOXEPIN; PALLADIUM;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

CATALYSIS; LIGNANS; MODELS, MOLECULAR; PALLADIUM; STEREOISOMERISM;

EID: 84874886242     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201209868     Document Type: Article

References (56)

1. T. J. Schmidt, S. Vossing, M. Klaes, S. Grimme, Planta Med. 2007, 73, 1574-1580.
2. L. F. Tietze, M. A. Düfert, S. C. Schild, General Principles of Diastereoselective Reactions: Diastereoselective Domino Reactions in Comprehensive Chirality, Vol. 2 (Eds.:, E. M. Carreira, H. Yamamoto,), Amsterdam, Elsevier, 2012, pp. 97-12
3. L. F. Tietze, S. Stewart, M. A. Düfert, Domino Reactions in the Enantioselective Synthesis of Bioactive Natural Products in Modern Tools for the Synthesis of Complex Bioactive Molecules (Eds.:, J. Cossy, S. Arseniyades,), Wiley, Hoboken, 2012
4. H. Pellissier, Adv. Synth. Catal. 2012, 354, 237-294
5. S. Giboulot, F. Liron, G. Prestat, B. Wahl, M. Sauthier, Y. Castanet, A. Montreux, G. Poli, Chem. Commun. 2012, 48, 5889-5891
6. M. Platon, R. Amardeil, L. Djakovitch, J.-C. Hierso, Chem. Soc. Rev. 2012, 41, 3929-3968
7. L. F. Tietze, A. Düfert, Pure Appl. Chem. 2010, 82, 1375-1392
8. L. F. Tietze, A. Düfert, Domino Reactions Involving Catalytic Enantioselective Conjugate Additions in Catalytic Asymmetric Conjugate Reactions (Ed.:, A. Cordova,), Wiley-VCH, Weinheim, 2010, p. 321-350
9. C. Grondall, M. Jeanty, D. Enders, Nat. Chem. 2010, 2, 167-178
10. L. F. Tietze, L. Levy, The Mizoroki-Heck Reaction in Domino Processes in The Mizoroki-Heck Reaction (Ed.:, M. Oestreich,), Wiley-VCH, Chichester, 2008, p. 281-344
11. L. F. Tietze, G. Brasche, K. M. Gericke, Domino Reactions in Organic Synthesis, Wiley-VCH, Weinheim, 2006
12. K. C. Nicolaou, D. J. Edmonds, P. G. Bulger, Angew. Chem. 2006, 118, 7292-7344
13. Angew. Chem. Int. Ed. 2006, 45, 7134-7186
14. L. F. Tietze, Chem. Rev. 1996, 96, 115-136
15. L. F. Tietze, U. Beifuss, Angew. Chem. 1993, 105, 137-170
16. Angew. Chem. Int. Ed. Engl. 1993, 32, 131-163.
17. L. F. Tietze, T. Hungerland, M. A. Düfert, I. Objartel, D. Stalke, Chem. Eur. J. 2012, 18, 3286-3291
18. L. F. Tietze, T. Hungerland, C. Depken, C. Maaß, D. Stalke, Synlett 2012, 2516-2520
19. H. Liu, M. El-Salfiti, M. Lautens, Angew. Chem. 2012, 124, 9984-9988
20. Angew. Chem. Int. Ed. 2012, 51, 9846-9850
21. K. Parthasarathy, H. Han, C. Prakash, C.-H. Cheng, Chem. Commun. 2012, 48, 6580-6582
22. B. Yao, Q. Wang, J. Zhu, Angew. Chem. 2012, 124, 12477-12481
23. Angew. Chem. Int. Ed. 2012, 51, 12311-12315
24. A. Lasikova, J. Dohanosova, L. Hlavinova, M. Toffano, G. Vo-Thanh, J. Kozisek, T. Gracza, Tetrahedron: Asymmetry 2012, 23, 818-827
25. L. Mahendar, J. Krishna, A. G. K. Reddy, B. V. Ramulu, G. Satyanarayana, Org. Lett. 2012, 14, 628-631
26. B. Seashore-Ludlow, J. Danielsson, P. Somfai, Adv. Synth. Catal. 2012, 354, 205-216
27. T. Vlaar, E. Ruijter, R. V. A. Orru, Adv. Synth. Catal. 2011, 353, 809-841
28. B.-S. Kim, S.-Y. Lee, S.-W. Youn, Chem. Asian J. 2011, 6, 1952-1957
29. Y. Luo, X.-L. Pan, J. Wu, Org. Lett. 2011, 13, 1150-1153
30. M. Leibeling, D. C. Koester, M. Pawliczek, S. C. Schild, D. B. Werz, Nat. Chem. Biol. 2010, 6, 199-201
31. B. M. Trost, B. M. O'Boyle, D. Hund, Chem. Eur. J. 2010, 16, 9772-9776
32. T. Saget, N. Cramer, Angew. Chem. 2010, 122, 9146-9149
33. Angew. Chem. Int. Ed. 2010, 49, 8962-8965
34. L. F. Tietze, A. Düfert, F. Lotz, L. Sölter, K. Oum, T. Lenzer, T. Beck, R. Herbst-Irmer, J. Am. Chem. Soc. 2009, 131, 17879-17884
35. V. K. Aggarwal, P. W. Davies, A. T. Schmidt, Chem. Commun. 2004, 1232-1233.
36. 6 is commercially available but is also easily accessible by bromination of isovanillin:, J. E. Toth, P. R. Hamann, P. L. Fuchs, J. Org. Chem. 1988, 53, 4694-4708.
37. J. M. Beierlein, K. M. Frey, D. B. Bolstadt, P. M. Pelphrey, T. M. Joska, A. E. Smith, N. D. Priestley, D. L. Wright, A. C. Anderson, J. Med. Chem. 2008, 51, 7532-7540.
38. Synthesis of 5-iodobenzo[d][1,3]dioxole-4-carbaldehyde by an improved procedure:, R. J. Mattson, C. P. Sloan, C. C. Lockhart, J. D. Catt, Q. Gao, S. Huang, J. Org. Chem. 1999, 64, 8004-8007.
39. S.-M. Lu, H. Alper, J. Am. Chem. Soc. 2005, 127, 14776-14784.
40. L. F. Tietze, K. Kahle, T. Raschke, Chem. Eur. J. 2002, 8, 401-407
41. L. F. Tietze, K. Thede, R. Schimpf, F. Sannicolo, Chem. Commun. 2000, 583-584
42. L. F. Tietze, A. Modi, Eur. J. Org. Chem. 2000, 1959-1964.
43. A. Chieffi, K. Kamikawa, J. Ahman, J. M. Fox, S. L. Buchwald, Org. Lett. 2001, 3, 1897-1900
44. S. Buchwald, D. W. Old, J. P. Wolfe, M. Palucki, K. Kamikawa, A. Chieffi, J. P. Sadighi, R. A. Singer, J. Ahman, PCT Int. Appl., 2000, WO 2000002887A2 20000120
45. A. Renaudat, L. Jean-Gerard, R. Jazzar, C. E. Kefalidis, E. Clot, O. Baudoin, Angew. Chem. 2010, 122, 7419-7423
46. Angew. Chem. Int. Ed. 2010, 49, 7261-7265.
47. For the use of Sudan dyes in ozonolysis, see:, T. Veysoglu, L. A. Mitscher, J. K. Swayze, Synthesis 1980, 807-810.
48. T. Kottke, D. Stalke, J. Appl. Crystallogr. 1993, 26, 615-619
49. Bruker, SAINT V7.68A, Bruker AXS Inc., Madison (WI, USA), 2005
50. G. M. Sheldrick, SADABS 2012/1, Göttingen, 2012
51. G. M. Sheldrick, Acta Crystallogr. Sect. A 2008, 64, 112-122
52. C. B. Hübschle, G. M. Sheldrick, B. Dittrich, J. Appl. Crystallogr. 2011, 44, 1281-1284.
53. CCDC 913693 (1) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.
54. H. Flack, Acta Crystallogr. Sect. A 1983, 39, 876-881
55. H. Flack, G. Bernardinelli, J. Appl. Crystallogr. 2000, 33, 1143-1148
56. S. Parsons, H. Flack, Acta Crystallogr. Sect. A 2004, 60, s 61.