Collective total synthesis of englerin A and B, orientalol e and F, and oxyphyllol: Application of the organocatalytic [4+3] cycloaddition reaction

Chemistry - A European Journal

Volumn 19, Issue 7, 2013, Pages 2539-2547

  Wang, Jie ^a   Chen, Shu Guang ^b   Sun, Bing Feng ^a   Lin, Guo Qiang ^a   Shang, Yong Jia ^b  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

^b ANHUI NORMAL UNIVERSITY   (China)

Author keywords

anticancer; biosynthesis; cycloaddition; englerin A; total synthesis

Indexed keywords

ALLYLIC ALCOHOL; ANTICANCER; AZULENES; BIOLOGICAL EVALUATION; BIOSYNTHETIC PATHWAY; C-C BONDS; CYCLOADDITION REACTION; ENGLERIN A; HECK REACTIONS; NATURAL PRODUCTS; ORGANOCATALYTIC; PHYLLANTHUS; REDUCTION SEQUENCE; REGIO-SELECTIVE; RENAL CELL CARCINOMA; STEREO-SELECTIVE; TOTAL SYNTHESIS;

BIOCHEMISTRY; BIOSYNTHESIS; CYCLOADDITION; REGIOSELECTIVITY; SYNTHESIS (CHEMICAL);

STEREOSELECTIVITY;

ANTINEOPLASTIC AGENT; BIOLOGICAL PRODUCT; ENGLERIN A; ENGLERIN B; ORIENTALOL E; ORIENTALOL F; SESQUITERPENE;

ARTICLE; CATALYSIS; CHEMISTRY; CYCLIZATION; CYCLOADDITION; KIDNEY CARCINOMA; OXIDATION REDUCTION REACTION; STEREOISOMERISM; SYNTHESIS;

ANTINEOPLASTIC AGENTS, PHYTOGENIC; BIOLOGICAL AGENTS; CARCINOMA, RENAL CELL; CATALYSIS; CYCLIZATION; CYCLOADDITION REACTION; OXIDATION-REDUCTION; SESQUITERPENES, GUAIANE; STEREOISOMERISM;

EID: 84873343839     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201203467     Document Type: Article

References (55)

1. E. Breitmaier, Terpenes, Wiley-VCH, Weinheim, 2006, ISBN: 3 -527-31786-4.
2. L. H. Miller, X. Su, Cell 2011, 146, 855
3. World Health Organization, Guidelines for the Treatment of Malaria, World Health Organization Press, Geneva, 2006.
4. K. C. Nicolaou, T. Montagnon, in Molecules that Changed the World, Wiley-VCH, Weinheim, 2008, p. 207.
5. P. A. Wender, J.-M. Kee, J.-M. Warrington, Science 2008, 320, 649.
6. A. Ghantous, H. Gali-Muhtasib, H. Vuorela, N. A. Saliba, N. Darwiche, Drug Discovery Today 2010, 15, 668.
7. R. Ratnayake, D. Covell, T. T. Ransom, K. R. Gustafson, J. A. Beutler, Org. Lett. 2009, 11, 57.
8. R. Siegel, E. Ward, O. Brawley, A. Jemal, Ca-Cancer J. Clin. 2011, 61, 212.
9. W. J. Chain, Synlett 2011, 2605
10. R. H. Pouwer, J. A. Richard, C. C. Tseng, D. Y. K. Chen, Chem. Asian J. 2012, 7, 22
11. Y. Lu, H. Yao, B. Sun, Chin. J. Org. Chem. 2012, 32, 1-12; for total syntheses, see
12. M. Willot, L. Radtke, D. Konning, R. Frohlich, V. H. Gessner, C. Strohmann, M. Christmann, Angew. Chem. 2009, 121, 9269
13. Angew. Chem. Int. Ed. 2009, 48, 9105
14. Q. Zhou, X. Chen, D. Ma, Angew. Chem. 2010, 122, 3591
15. Angew. Chem. Int. Ed. 2010, 49, 3513
16. K. Molawi, N. Delpont, A. M. Echavarren, Angew. Chem. 2010, 122, 3595
17. Angew. Chem. Int. Ed. 2010, 49, 3517
18. K. C. Nicolaou, Q. A. Kang, S. Y. Ng, D. Y. K. Chen, J. Am. Chem. Soc. 2010, 132, 8219
19. Z. Li, M. Nakashige, W. J. Chain, J. Am. Chem. Soc. 2011, 133, 6553; for formal total syntheses, see
20. J. Xu, E. J. Caro-Diaz, E. A. Theodorakis, Org. Lett. 2010, 12, 3708
21. C. L. Wang, B. F. Sun, S. G. Chen, R. Ding, G. Q. Lin, J. Y. Xu, Y. J. Shang, Synlett 2012, 263
22. J. Lee, K. A. Parker, Org. Lett. 2012, 14, 2682
23. P. Gao, S. P. Cook, Org. Lett. 2012, 14, 3340; for synthetic studies, see
24. V. Navickas, D. B. Ushakov, M. E. Maier, M. Strobele, H. J. Meyer, Org. Lett. 2010, 12, 3418
25. D. B. Ushakov, V. Navickas, M. Strobele, C. Maichle-Mossmer, F. Sasse, M. E. Maier, Org. Lett. 2011, 13, 2090
26. B. F. Sun, C. L. Wang, R. Ding, J. Y. Xu, G. Q. Lin, Tetrahedron Lett. 2011, 52, 2155.
27. K. P. Chan, D. Y. K. Chen, ChemMedChem 2011, 6, 420
28. L. Radtke, M. Willot, H. Y. Sun, S. Ziegler, S. Sauerland, C. Strohmann, R. Frohlich, P. Habenberger, H. Waldmann, M. Christmann, Angew. Chem. 2011, 123, 4084
29. Angew. Chem. Int. Ed. 2011, 50, 3998
30. R. K. Akee, T. Ransom, R. Ratnayake, J. B. McMahon, J. A. Beutler, J. Nat. Prod. 2012, 75, 459
31. J. Xu, E. J. Caro-Diaz, A. Batova, S. D. Sullivan, E. A. Theodorakis, Chem. Asian J. 2012, 7, 1052.
32. G.-P. Peng, G. Tian, X.-F. Huang, F.-C. Lou, Phytochemistry 2003, 63, 877.
33. S. Sutthivaiyakit, N. N. Nakorn, W. Kraus, P. Sutthivaiyakit, Tetrahedron 2003, 59, 9991.
34. For a total synthesis of orientalol F, see:, E. Jiménez- Núñez, K. Molawi, A. M. Echavarren, Chem. Commun. 2009, 7327.
35. M. Harmata, S. K. Ghosh, X. Hong, S. Wacharasindhu, P. Kirchhoefer, J. Am. Chem. Soc. 2003, 125, 2058.
36. M. Ohno, K. Mori, T. Hattori, S. Eguchi, J. Org. Chem. 1990, 55, 6086.
37. P. Weyerstahl, J. Brendel, Liebigs Ann. Chem. 1988, 1015.
38. K. A. Ahrendt, C. J. Borths, D. W. C. MacMillan, J. Am. Chem. Soc. 2000, 122, 4243
39. A. B. Northrup, D. W. C. MacMillan, J. Am. Chem. Soc. 2002, 124, 2458.
40. Z.-S. Su, S. Yin, Z.-W. Zhou, Y. Wu, J. Ding, J.-M. Yue, J. Nat. Prod. 2008, 71, 1410-1413; for a possible application in phorbol synthesis, see
41. K. Lee, J. K. Cha, J. Am. Chem. Soc. 2001, 123, 5590.
42. R. S. Lenox, J. A. Katzenellenbogen, J. Am. Chem. Soc. 1973, 95, 957.
43. Handbook of C-H Transformations (Ed.:, G. Dyker,), Wiley-VCH, Weinheim, 2005
44. A. R. Dick, M. S. Sanford, Tetrahedron 2006, 62, 2439
45. M. S. Chen, M. C. White, Science 2007, 318, 783; for innate and guided C-H functionalization, see
46. T. BrÜckl, R. D. Baxter, Y. Ishihara, P. S. Baran, Acc. Chem. Res. 2012, 45, 826, and references therein; for guided desaturation of unactivated aliphatics, see
47. A.-F. Voica, A. Mendoza, W. R. Gutekunst, J. O. Fraga, P. S. Bara, Nat. Chem. 2012, 4, 629.
48. S. Maki, K. Konno, H. Takayama, Tetrahedron Lett. 1997, 38, 7067.
49. R. Mello, M. Fiorentino, C. Fusco, R. Curci, J. Am. Chem. Soc. 1989, 111, 6749.
50. A. Tenaglia, E. Terranova, B. Waegell, Tetrahedron Lett. 1989, 30, 5271.
51. S. Lee, P. L. Fuchs, J. Am. Chem. Soc. 2002, 124, 13978.
52. L. I. Krimen, D. J. Cota, Org. React. 1969, 17, 213.
53. M. Willot, M. Christmann, Nat. Chem. 2010, 2, 519.
54. J. H. G. Lago, C. B. Brochini, N. F. Roque, Phytochemistry 2000, 55, 727.
55. CCDC-846445 (16′) 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.