Enantioselective photocycloaddition of 3-hydroxyflavones: Total syntheses and absolute configuration assignments of (+)-ponapensin and (+)-elliptifoline

Journal of the American Chemical Society

Volumn 134, Issue 31, 2012, Pages 13108-13113

  Lajkiewicz, Neil J ^a   Roche, Stéphane P ^a   Gerard, Baudouin ^a   Porco, John A ^a  

^a Boston University   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ABSOLUTE CONFIGURATION; CINNAMATES; CYCLOADDUCTS; DIPOLAROPHILES; ENANTIOSELECTIVE; ENANTIOSELECTIVE SYNTHESIS; NATURAL PRODUCTS; PHOTOCYCLOADDITION; TOTAL SYNTHESIS;

BIOMIMETICS;

ENANTIOSELECTIVITY;

3 HYDROXYFLAVONE; ELLIPTIFOLINE; PONAPENSIN; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; CYCLOADDITION; DRUG STRUCTURE; DRUG SYNTHESIS; ENANTIOSELECTIVITY; PHOTOCHEMISTRY;

BENZOFURANS; FLAVONOIDS; HETEROCYCLIC COMPOUNDS, 3-RING; MOLECULAR CONFORMATION; OXIDATION-REDUCTION; PHOTOCHEMICAL PROCESSES; PYRROLES; STEREOISOMERISM;

EID: 84864675937     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja305342f     Document Type: Article

References (58)

1. Ko, F.-N.; Wu, T.-S.; Liou, M.-J.; Huang, T.-F.; Teng, C.-M. Eur. J. Pharmacol. 1992, 218, 129-135
2. Hwang, B. Y.; Su, B.; Chai, H.; Mi, Q.; Kardono, L. B.; Afriastini, J. J.; Riswan, S.; Santarsiero, B. D.; Mesecar, A. D.; Wild, R.; Fairchild, C. R.; Vite, G. D.; Rose, W. C.; Farnsworth, N. R.; Cordell, G. A.; Pezzuto, J. M.; Swanson, S. M.; Kinghorn, A. D. J. Org. Chem. 2004, 69, 3350-3358
3. Salim, A. A.; Pawlus, A. D.; Chai, H.-B.; Farnsworth, N. R.; Kinghorn, A. D.; Carcache-Blanco, E. J. Bioorg. Med. Chem. Lett. 2007, 17, 109-112
4. Wang, S.-K.; Cheng, Y. J.; Duh, C.-Y. J. Nat. Prod. 2001, 64, 92-94
5. King, M. L.; Chiang, C. C.; Ling, H.-C.; Fujita, E.; Ochiai, M.; McPhail, A. T. J. Chem. Soc., Chem. Commun. 1982, 1150-1151
6. Dumontet, V.; Thoison, O.; Omobuwajo, O. R.; Martin, M.-T.; Perromat, G.; Chiaroni, A.; Riche, C.; Päs, M.; Sévenet, T.; Hadi, A. H. Tetrahedron 1996, 52, 6931-6942
7. Inada, A.; Sorano, T.; Murata, H.; Inatomi, Y.; Darnaedi, D.; Nakanishi, T. Chem. Pharm. Bull. 2001, 49, 1226-1228
8. Ebada, S. S.; Lajkiewicz, N.; Porco, J. A., Jr.; Li-Weber, M.; Proksch, P. Prog. Chem. Org. Nat. Prod. 2011, 94, 1-58
9. Ribeiro, N.; Thuaud, F.; Nebigil, C.; Désaubry, L. Bioorg. Med. Chem. 2012, 20, 1857-1864
10. Thuaud, F.; Ribeiro, N.; Gaiddon, C.; Cresteil, T.; Désaubry, L. J. Med. Chem. 2011, 54, 411-415
11. Rodrigo, C. M.; Cencic, R.; Roche, S. P.; Pelletier, J.; Porco, J. A., Jr. J. Med. Chem. 2012, 55, 558-562
12. Malona, J. A.; Cariou, K.; Spencer, W. T.; Frontier, A. J. J. Org. Chem. 2012, 77, 1891-1908
13. Magnus, P.; Freund, W. A.; Moorhead, E. J.; Rainey, T. J. Am. Chem. Soc. 2012, 134, 6140-6142
14. Gerard, B.; Sangji, S.; OLeary, D.; Porco, J. A., Jr. J. Am. Chem. Soc. 2006, 128, 7754-7756
15. Gerard, B.; Cencic, R.; Pelletier, J.; Porco, J. A., Jr. Angew. Chem., Int. Ed. 2007, 46, 7831-7834
16. Roche, S. P.; Cencic, R.; Pelletier, J.; Porco, J. A., Jr. Angew. Chem., Int. Ed. 2010, 49, 6533-6538
17. Tsuda, Y.; Sakai, Y.; Akiyama, K.; Isobe, K. Chem. Pharm. Bull. 1991, 39, 2120-2123
18. Schoop, A.; Greiving, H.; Göhrt, A. Tetrahedron Lett. 2000, 41, 1913-1916
19. Hoveyda, A. H.; Evans, D. A.; Fu, G. C. Chem. Rev. 1993, 93, 1307-1370
20. Gribble, G. W. Org. Process Res. Dev. 2006, 10, 1062-1075
21. Saksena, A. K.; Mangiaracina, P. Tetrahedron Lett. 1983, 24, 273-276
22. Bürgi, H. B.; Dunitz, J. D.; Shefter, E. J. Am. Chem. Soc. 1973, 95, 5065-5067
23. Lodge, E. P.; Heathcock, C. H. J. Am. Chem. Soc. 1987, 109, 2819-2820
24. Gerard, B.; Jones, G., II; Porco, J. A., Jr. J. Am. Chem. Soc. 2004, 126, 13620-13621
25. Moncrief, J. W.; Sims, S. P. Chem. Commun. 1969, 914-915
26. Flack, H. D.; Bernardinelli, G. Acta Crystallogr., Sect. A 1999, 55, 908-915
27. Frackenpohl, J.; Adelt, I.; Antonicek, H.; Arnold, C.; Behrmann, P.; Blaha, N.; Böhmer, J.; Gutbrod, O.; Hanke, R.; Hohmann, S.; Van Houtdreve, M.; Lösel, P.; Malsam, O.; Melchers, M.; Neufert, V.; Peschel, E.; Reckmann, U.; Schenke, T.; Thiesen, H.-P.; Velten, R.; Vogelsang, K.; Weiss, H.-C. Bioorg. Med. Chem. 2009, 17, 4160-4184
28. Herzon, S. B.; Calandra, N. A.; King, S. M. Angew. Chem., Int. Ed. 2011, 50, 8863-8866
29. Watanabe, T.; Takeuchi, T.; Kohzuma, S.; Umezawa, K.; Otsuka, M. Chem. Commun. 1998, 1097-1098
30. Otera, J.; Danoh, N.; Nozaki, H. J. Org. Chem. 1991, 56, 5307-5311
31. Otera, J. Chem. Rev. 1993, 93, 1449-1470
32. Otera, J. Acc. Chem. Res. 2004, 37, 288-296
33. Lipton, M. F.; Basha, A.; Weinreb, S. M. Org. Synth., Coll. 1980, 59, 49-53
34. Eldred, S. E.; Stone, D. A.; Gellman, S. H.; Stahl, S. S. J. Am. Chem. Soc. 2003, 125, 3422-3423
35. Han, C.; Lee, J. P.; Lobkovsky, E.; Porco, J. A., Jr. J. Am. Chem. Soc. 2005, 127, 10039-10044
36. Ohshima, T.; Iwasaki, T.; Mashima, K. Chem. Commun. 2006, 2711-2713
37. Sim, T. B.; Yoon, N. M. Synlett 1994, 827-828
38. Pirrung, M. C.; Chau, J. H.-L. J. Org. Chem. 1995, 60, 8084-8085
39. Buller, M. J.; Gilley, C. B.; Nguyen, B.; Olshansky, L.; Fraga, B.; Kobayashi, Y. Synlett 2008, 15, 2244-2248
40. King, F. D.; Caddick, S. Org. Biomol. Chem. 2011, 9, 4361-4366
41. Speckamp, W. N.; Moolenaar, M. J. Tetrahedron 2000, 56, 3817-3856
42. Thomas, K. M.; Naduthambi, D.; Zondlo, N. J. J. Am. Chem. Soc. 2006, 128, 2216-2217
43. Sui, Q.; Borchardt, D.; Rabenstein, D. L. J. Am. Chem. Soc. 2007, 129, 12042-12048
44. 1,3 strain in acyliminiums, see: Hart, D. J. J. Am. Chem. Soc. 1980, 102, 397-398
45. Nagase, H.; Yamamoto, N.; Nemoto, T.; Yoza, K.; Kamiya, K.; Hirono, S.; Momen, S.; Izumimoto, N.; Hasebe, K.; Mochizuki, H.; Fujii, H. J. Org. Chem. 2008, 73, 8093-8096
46. Mersmann, S.; Raabe, G.; Bolm, C. Tetrahedron Lett. 2011, 52, 5424-5426
47. Bacher, M.; Hofer, O.; Brader, G.; Vajrodaya, S.; Greger, H. Phytochemistry 1999, 52, 253-263
48. Proksch, P.; Edrada, R.; Ebel, R.; Bohnenstengel, F. I.; Nugroho, B. W. Curr. Org. Chem. 2001, 5, 923-938
49. Nakazaki, M.; Chikamatsu, H.; Naemura, K.; Nishino, M.; Murakami, H.; Asao, M. J. Org. Chem. 1979, 44, 4588-4593
50. Truppo, M. D.; Kim, J.; Brower, M.; Madin, A.; Sturr, M. G.; Moore, J. C. J. Mol. Catal. B: Enzym. 2006, 38, 158-162
51. Takahashi, S.; Kuzuyama, T.; Watanabe, H.; Seto, H. Proc. Natl. Acad. Sci. U.S.A. 1998, 95, 9879-9884
52. OConnor, S. E.; Maresh, J. J. Nat. Prod. Rep. 2006, 23, 532-547
53. Munos, J. W.; Pu, X.; Mansoorabadi, S. O.; Kim, H. J.; Liu, H.-W. J. Am. Chem. Soc. 2009, 131, 2048-2049
54. Fung, P. K.; Krushkal, J.; Weathers, P. J. Chem. Biodivers. 2010, 7, 1098-1110
55. Bastian, S.; Liu, X.; Meyerowitz, J. T.; Snow, C. D.; Chen, M. M. Y.; Arnold, F. H. Metab. Eng. 2011, 13, 345-352
56. Bertozzi, F.; Crotti, P.; Macchia, F.; Pineschi, M.; Feringa, B. L. Angew. Chem., Int. Ed. 2001, 40, 930-932
57. Dehli, J. R.; Gotor, V. Chem. Soc. Rev. 2002, 31, 365-370
58. Miller, L. C.; Sarpong, R. Chem. Soc. Rev. 2011, 40, 4550-4562