Convergent Assembly of the Tetracyclic Meroterpenoid (−)-Cyclosmenospongine by a Non-Biomimetic Polyene Cyclization

Angewandte Chemie - International Edition

Volumn 55, Issue 45, 2016, Pages 14131-14135

  Speck, Klaus ^a   Wildermuth, Raphael ^a   Magauer, Thomas ^a  

^a UNIVERSITY OF MUNICH   (Germany)

Author keywords

cations; cyclization; natural products; terpenoids; total synthesis

Indexed keywords

BIOMIMETICS; BIOSYNTHESIS; LIPIDS; MACHINERY; POSITIVE IONS;

ENOL ETHERS; NATURAL PRODUCTS; STEREOCENTERS; TERPENOIDS; TOTAL SYNTHESIS;

CYCLIZATION;

EID: 84992448670     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201608040     Document Type: Article

References (64)

1. K. U. Wendt, G. E. Schulz, E. J. Corey, D. R. Liu, Angew. Chem. Int. Ed. 2000, 39, 2812–2833;
2. Angew. Chem. 2000, 112, 2930–2952;
3. M. Baunach, J. Franke, C. Hertweck, Angew. Chem. Int. Ed. 2015, 54, 2604–2626;
4. Angew. Chem. 2015, 127, 2640–2664;
5. E. Oldfield, F.-Y. Lin, Angew. Chem. Int. Ed. 2012, 51, 1124–1137;
6. Angew. Chem. 2012, 124, 1150–1163;
7. S. Lodeiro, Q.-B. Xiong, W. K. Wilson, M. D. Kolesnikova, C. S. Onak, S. P. T. Matsuda, J. Am. Chem. Soc. 2007, 129, 11213–11222;
8. D. W. Christianson, Chem. Rev. 2006, 106, 3412–3442;
9. D. E. Cane, Chem. Rev. 1990, 90, 1089–1103.
10. For an overview, see:
11. K. Ishihara in From Biosynthesis to Total Synthesis, Wiley, Hoboken, 2016, pp. 296–330;
12. R. A. Yoder, J. N. Johnston, Chem. Rev. 2005, 105, 4730–4756;
13. W. S. Johnson, Angew. Chem. Int. Ed. Engl. 1976, 15, 9–17;
14. Angew. Chem. 1976, 88, 33–41.
15. For recent examples, see:
16. O. F. Jeker, A. G. Kravina, E. M. Carreira, Angew. Chem. Int. Ed. 2013, 52, 12166–12169;
17. Angew. Chem. 2013, 125, 12388–12391;
18. Y. Tian, X. Xu, L. Zhang, J. Qu, Org. Lett. 2016, 18, 268–271;
19. G. Rajendar, E. J. Corey, J. Am. Chem. Soc. 2015, 137, 5837–5844;
20. S. V. Pronin, R. A. Shenvi, Nat. Chem. 2012, 4, 915–920;
21. Q. Zhang, K. Tiefenbacher, Nat. Chem. 2015, 7, 197–202;
22. M. J. Geier, M. R. Gagné, J. Am. Chem. Soc. 2014, 136, 3032–3035;
23. Z. Yang, H. Li, L. Zhang, M.-T. Zhang, J.-O. Cheng, S. Luo, Chem. Eur. J. 2015, 21, 14723–14727;
24. M. A. Schafroth, D. Sarlah, S. Krautwald, E. M. Carreira, J. Am. Chem. Soc. 2012, 134, 20276–20278;
25. S. Rendler, D. W. C. MacMillan, J. Am. Chem. Soc. 2010, 132, 5027–5029;
26. S. G. Sethofer, T. Mayer, F. D. Toste, J. Am. Chem. Soc. 2010, 132, 8276–8277;
27. K. Surendra, E. J. Corey, J. Am. Chem. Soc. 2012, 134, 11992–11994;
28. R. R. Knowles, S. Li, E. N. Jacobsen, J. Am. Chem. Soc. 2010, 132, 5030–5032.
29. R. Wildermuth, K. Speck, T. Magauer, Synthesis 2016, 1814–1824;
30. C. L. Hugelshofer, T. Magauer, J. Am. Chem. Soc. 2016, 138, 6420–6423;
31. C. L. Hugelshofer, T. Magauer, J. Am. Chem. Soc. 2015, 137, 3807–3810.
32. N. K. Utkina, V. A. Denisenko, O. V. Scholokova, M. V. Virovaya, N. G. Prokof'eva, Tetrahedron Lett. 2003, 44, 101–102;
33. N. K. Utkina, V. A. Denisenko, O. V. Scholokova, A. E. Makarchenko, J. Nat. Prod. 2003, 66, 1263–1265.
34. N. G. Prokof'eva, N. K. Utkina, E. L. Chaikina, A. E. Makarchenko, Comp. Biochem. Physiol. Part B 2004, 139, 169–173;
35. K. Minagawa, S. Kouzuki, J. Yoshimoto, Y. Kawamura, H. Tani, T. Iwata, Y. Terui, H. Nakai, S. Yagi, N. Hattori, T. Fujiwara, T. Kamigauchi, J. Antibiot. 2002, 55, 155–164;
36. A. E. Wright, S. A. Rueth, S. S. Cross, J. Nat. Prod. 1991, 54, 1108–1111;
37. H. Prawat, C. Mahidol, W. Kaweetripob, S. Wittayalai, S. Ruchirawat, Tetrahedron 2012, 68, 6881–6886.
38. For recent syntheses of related members, see:
39. K. K. W. Kuan, H. P. Pepper, W. M. Bloch, J. H. George, Org. Lett. 2012, 14, 4710–4713;
40. A. Rosales, J. Muñoz-Bascón, E. Roldan-Molina, N. Rivas-Bascón, N. M. Padial, R. Rodríguez-Maecker, I. Rodríguez-García, J. E. Oltra, J. Org. Chem. 2015, 80, 1866–1870;
41. K. Watanabe, J. Sakurai, H. Abe, T. Katoh, Chem. Commun. 2010, 46, 4055–4057;
42. J. Sakurai, T. Kikuchi, O. Takahashi, K. Watanabe, T. Katoh, Eur. J. Org. Chem. 2011, 2948–2957;
43. T. Taishi, S. Takechi, S. Mori, Tetrahedron Lett. 1998, 39, 4347–4350;
44. I. S. Marcos, A. Conde, R. F. Moro, P. Basabe, D. Díez, J. G. Urones, Tetrahedron 2010, 66, 8280–8290;
45. M. Gordaliza, Mar. Drugs 2012, 10, 358–402.
46. K. Speck, K. Karaghiosoff, T. Magauer, Org. Lett. 2015, 17, 1982–1985.
47. A. G. Myers, L. McKinstry, J. Org. Chem. 1996, 61, 2428–2440.
48. S. Wang, P. Li, L. Yu, L. Wang, Org. Lett. 2011, 13, 5968–5971.
49. S. R. Chemler, D. Trauner, S. J. Danishefsky, Angew. Chem. Int. Ed. 2001, 40, 4544–4568;
50. Angew. Chem. 2001, 113, 4676–4701;
51. A. J. J. Lennox, G. C. Lloyd-Jones, Chem. Soc. Rev. 2014, 43, 412–443.
52. N. C. Bruno, S. L. Buchwald, Chem. Sci. 2013, 4, 916–920;
53. T. E. Barder, S. D. Walker, J. R. Martinelli, S. L. Buchwald, J. Am. Chem. Soc. 2005, 127, 4685–4696.
54. C. Bucher, R. M. Deans, N. Z. Burns, J. Am. Chem. Soc. 2015, 137, 12784–12787.
55. E. J. Corey, D. D. Staas, J. Am. Chem. Soc. 1998, 120, 3526–3527.
56. For related thioenol ether cyclizations, see:
57. T. A. Blumenkopf, M. Bratz, A. Castañeda, G. C. Look, L. E. Overman, D. Rodriguez, A. S. Thompson, J. Am. Chem. Soc. 1990, 112, 4386–4399;
58. H. Kusama, R. Hara, S. Kawahara, T. Nishimori, H. Kashima, N. Nakamura, K. Morihira, I. Kuwaijima, J. Am. Chem. Soc. 2000, 122, 3811–3820;
59. P. K. Sasmal, M. E. Maier, J. Org. Chem. 2003, 68, 824–831;
60. P. K. Sasmal, M. E. Maier, Org. Lett. 2002, 4, 1271–1274.
61. V. Lakshmi, S. P. Gunasekera, F. J. Schmitz, X. Ji, D. van der Helm, J. Org. Chem. 1990, 55, 4709–4711.
62. M. Nakamura, A. Suzuki, M. Nakatani, T. Fuchikami, M. Inoue, T. Katoh, Tetrahedron Lett. 2002, 43, 6929–6932.
63. R. J. Capon, J. Nat. Prod. 1990, 53, 753–756.
64. CCDC 1499443 (18) and 1499442 (1) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre.