Concise Total Synthesis of Dehaloperophoramidine

Angewandte Chemie - International Edition

Volumn 55, Issue 5, 2016, Pages 1801-1804

  Popov, Kirill ^a   Hoang, Anita ^a   Somfai, Peter ^a,b  

^a LUND UNIVERSITY   (Sweden)

^b UNIVERSITY OF TARTU   (Estonia)

Author keywords

alkaloids; domino reactions; heterocycles; natural products; total synthesis

Indexed keywords

ALKALOIDS; METABOLITES; MOLECULES; REACTION KINETICS;

DOMINO PROCESS; DOMINO REACTIONS; HETEROCYCLES; NATURAL PRODUCTS; TARGET MOLECULE; TOTAL SYNTHESIS;

SYNTHESIS (CHEMICAL);

FUSED HETEROCYCLIC RINGS; HALOGENATED HYDROCARBON; PEROPHORAMIDINE;

HUMAN; SYNTHESIS; TUMOR CELL LINE;

CELL LINE, TUMOR; HETEROCYCLIC COMPOUNDS, 4 OR MORE RINGS; HUMANS; HYDROCARBONS, HALOGENATED;

EID: 84955704958     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201510661     Document Type: Article

References (43)

1. K. C. Nicolaou, J. S. Chen, Classics in total synthesis III: further targets, strategies, methods, Wiley-VCH, Weinheim, 2011;
2. T. Hudlicky, J. W. Reed, The way of synthesis: evolution of design and methods for natural products, Wiley-VCH, Weinheim, 2007;
3. K. C. Nicolaou, D. Vourloumis, N. Winssinger, P. S. Baran, Angew. Chem. Int. Ed. 2000, 39, 44-122;
4. Angew. Chem. 2000, 112, 46-126.
5. J. B. Hendrickson, J. Am. Chem. Soc. 1975, 97, 5784-5800;
6. B. M. Trost, Science 1991, 254, 1471-1477;
7. T. Newhouse, P. S. Baran, R. W. Hoffmann, Chem. Soc. Rev. 2009, 38, 3010-3021;
8. P. A. Wender, B. L. Miller, Nature 2009, 460, 197-201;
9. T. Gaich, P. S. Baran, J. Org. Chem. 2010, 75, 4657-4673;
10. N. J. Green, M. S. Sherburn, Aust. J. Chem. 2013, 66, 267-283;
11. C. A. Kuttruff, M. D. Eastgate, P. S. Baran, Nat. Prod. Rep. 2014, 31, 419-432;
12. J. Mulzer, Nat. Prod. Rep. 2014, 31, 595-603;
13. P. A. Wender, Nat. Prod. Rep. 2014, 31, 433-440.
14. J. R. Fuchs, R. L. Funk, J. Am. Chem. Soc. 2004, 126, 5068-5069;
15. H. Wu, F. Xue, X. Xiao, Y. Qin, J. Am. Chem. Soc. 2010, 132, 14052-14054;
16. H. Zhang, L. Hong, H. Kang, R. Wang, J. Am. Chem. Soc. 2013, 135, 14098-14101;
17. B. M. Trost, M. Osipov, S. Kruger, Y. Zhang, Chem. Sci. 2015, 6, 349-353.
18. J. Yang, H. Wu, L. Shen, Y. Qin, J. Am. Chem. Soc. 2007, 129, 13794-13795;
19. P. Liu, J. H. Seo, S. M. Weinreb, Angew. Chem. Int. Ed. 2010, 49, 2000-2003;
20. Angew. Chem. 2010, 122, 2044-2047;
21. Z. Zuo, W. Xie, D. Ma, J. Am. Chem. Soc. 2010, 132, 13226-13228;
22. J. Belmar, R. L. Funk, J. Am. Chem. Soc. 2012, 134, 16941-16943.
23. A. Numata, C. Takahashi, Y. Ito, T. Takada, K. Kawai, Y. Usami, E. Matsumura, M. Imachi, T. Ito, T. Hasegawa, Tetrahedron Lett. 1993, 34, 2355-2358;
24. S. M. Verbitski, C. L. Mayne, R. A. Davis, G. P. Concepcion, C. M. Ireland, J. Org. Chem. 2002, 67, 7124-7126.
25. B. M. Trost, M. Osipov, Chem. Eur. J. 2015, 21, 16318-16343.
26. E. A. Peterson, L. E. Overman, Proc. Natl. Acad. Sci. USA 2004, 101, 11943-11948;
27. J. Christoffers, A. Baro, Quaternary Stereocenters: Challenges and Solutions for Organic Synthesis, Wiley-VCH, Weinheim, 2005.
28. A. Sabahi, A. Novikov, J. D. Rainier, Angew. Chem. Int. Ed. 2006, 45, 4317-4320;
29. Angew. Chem. 2006, 118, 4423-4426;
30. T. Ishida, H. Ikota, K. Kurahashi, C. Tsukano, Y. Takemoto, Angew. Chem. Int. Ed. 2013, 52, 10204-10207;
31. Angew. Chem. 2013, 125, 10394-10397.
32. T.-L. Ho, Symmetry: a basis for synthesis design, Wiley, New York, 1995.
33. L.-F. Tietze, G. Brasche, K. M. Gericke, Domino Reactions in Organic Synthesis, Wiley-VCH, Weinheim, 2006.
34. Y. Du, H. Wu, H. Song, Y. Qin, D. Zhang, Chin. J. Chem. 2012, 30, 1970-1973.
35. J. T. Link, L. E. Overman, J. Am. Chem. Soc. 1996, 118, 8166-8167.
36. T. Y. S. But, P. H. Toy, Chem. Asian J. 2007, 2, 1340-1355;
37. S. Fletcher, Org. Chem. Front. 2015, 2, 739-752.
38. The use of orthoamide to designate functionalities in literature is somewhat confusing. Herein we are adopting the IUPAC nomenclature. See: DOI: 10.1351/goldbook.O04332.
39. S. K. Bur, Top. Curr. Chem. 2007, 274, 125-171.
40. M. Tajbakhsh, R. Hosseinzadeh, H. Alinezhad, S. Ghahari, A. Heydari, S. Khaksar, Synthesis 2011, 490-496.
41. H. C. Brown, J. Chem. Soc. 1956, 1248-1268;
42. L. W. Haynes, A. G. Cook, in Enamines: synthesis, structure, and reactions, 2 nd ed., (Ed.: A. G. Cook,), Marcel Dekker, New York, 1988, pp. 103-163.
43. CCDC 1432648 (10) and 1432649 (ent- I) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre.