Pyrrole aminoimidazole alkaloid metabiosynthesis with marine sponges Agelas conifera and Stylissa caribica

Angewandte Chemie - International Edition

Volumn 51, Issue 20, 2012, Pages 4877-4881

  Stout, E Paige ^a   Wang, Yong Gang ^b   Romo, Daniel ^b   Molinski, Tadeusz F ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b TEXAS A AND M UNIVERSITY   (United States)

Author keywords

alkaloids; biosynthesis; electron transfer; metabiosynthesis; natural products

Indexed keywords

ALKALOIDS; BOND-FORMING REACTIONS; CELL-FREE; ELECTRON TRANSFER; ENZYME PREPARATION; MARINE SPONGE; METABIOSYNTHESIS; NATURAL PRODUCTS; SINGLE ELECTRON TRANSFER;

AROMATIC COMPOUNDS; BIOCHEMISTRY; BIOSYNTHESIS; ELECTRON TRANSITIONS; METABOLITES;

NITROGEN COMPOUNDS;

ALKALOID; IMIDAZOLE DERIVATIVE; PYRROLE DERIVATIVE;

AGELAS; ANIMAL; ARTICLE; BIOSYNTHESIS; CHEMISTRY; METABOLISM; SPONGE (PORIFERA); SYNTHESIS;

AGELAS; ALKALOIDS; ANIMALS; IMIDAZOLES; PORIFERA; PYRROLES;

EID: 84860876226     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201108119     Document Type: Article

References (54)

1. A. Aiello, E. Fattorusso, M. Menna, O. Taglialatela-Scafati, in Modern Alkaloids. Structure, Isolation, Synthesis and Biology (Eds.:, E. Fattorusso, O. Taglialatela-Scafati,), Wiley-VCH, Darmstadt, 2008. The possibility that PAIs are the products of bacterial consortia has not been excluded.
2. R. P. Walker, D. J. Faulkner, D. Van Engen, J. Clardy, J. Am. Chem. Soc. 1981, 103, 6772-6773.
3. V. S. Bernan, D. M. Roll, C. M. Ireland, M. Greenstein, W. M. Maiese, D. A. Steinberg, J. Antimicrob. Chemother. 1993, 32, 539-550
4. R. Rosa, W. Silva, G. E. de Motta, A. D. Rodríguez, J. J. Morales, M. Ortiz, Experientia 1992, 48, 885-887
5. A. D. Rodríguez, M. J. Lear, J. J. La Clair, J. Am. Chem. Soc. 2008, 130, 7256-7258
6. A. Cipres, D. P. O'Malley, K. Li, D. Finlay, P. S. Baran, K. Vuori, ACS Chem. Biol. 2010, 5, 195-202.
7. J. Kobayashi, Y. Ohizumi, H. Nakamura, Y. Hirata, Experientia 1986, 42, 1176-1177.
8. S. Forenza, L. Minale, R. Riccio, E. Fattorusso, J. Chem. Soc. Chem. Commun. 1971, 18, 1129-1130
9. E. E. Garcia, L. E. Benjamin, R. I. Fryer, J. Chem. Soc. Chem. Commun. 1973, 78-79.
10. J. J. Morales, A. D. Rodriguez, J. Nat. Prod. 1991, 54, 629-631.
11. T. Lindel, J. Hoffmann, M. Hochgürtel, J. R. Pawlik, J. Chem. Ecol. 2000, 26, 1477-1496.
12. J. Appenzeller, S. Tilvi, M. T. Martin, J. F. Gallard, H. Elbitar, E. T. H. Dau, C. Debitus, D. Laurent, C. Moriou, A. Al-Mourabit, Org. Lett. 2009, 11, 4874-4877.
13. T. Lindel, M. Hochgürtel, J. Org. Chem. 2000, 65, 2806-2809
14. M. R. Bhandari, R. Sivappa, C. J. Lovely, Org. Lett. 2009, 11, 1535-1538
15. Y. Wang, B. I. Morinaka, J. C. P. Reyes, J. H. Wolff, T. F. Molinski, D. Romo, J. Nat. Prod. 2010, 73, 428-434.
16. P. S. Baran, D. O'Malley, A. Zografos, Angew. Chem. 2004, 116, 2728-2731
17. Angew. Chem. Int. Ed. 2004, 43, 2674-2677
18. P. S. Baran, L. Zografos, D. O'Malley, J. Am. Chem. Soc. 2004, 126, 3726-3727
19. V. B. Birman, X. T. Jiang, Org. Lett. 2004, 6, 2369-2371.
20. D. Stien, G. T. Anderson, C. E. Chase, Y. H. Koh, S. M. Weinreb, J. Am. Chem. Soc. 1999, 121, 9574-9579
21. M. Movassaghi, D. S. Siegel, S. Han, Chem. Sci. 2010, 1, 561-566
22. For a comprehensive review of other agelastatin A syntheses, see, S. M. Weinreb, Nat. Prod. Rep. 2007, 24, 931-948.
23. I. B. Seiple, S. Su, I. S. Young, C. A. Lewis, J. Yamaguchi, P. S. Baran, Angew. Chem. 2010, 122, 1113-1116
24. Angew. Chem. Int. Ed. 2010, 49, 1095-1098
25. Angew. Chem. 2010, 122, 1113-1116
26. I. B. Seiple, S. Su, A. Nakamura, J. Yamaguchi, L. Jørgensen, R. A. Rodriguez, D. P. O'Malley, T. Gaich, M. Köch, P. S. Baran, J. Am. Chem. Soc. 2011, 133, 14710-14726.
27. R. B. Kinnel, H. P. Gehrken, R. Swali, G. Skoropowski, P. J. Scheuer, J. Org. Chem. 1998, 63, 3281-3286
28. K. S. Feldman, A. Y. Nuriye, Org. Lett. 2010, 12, 4532-4535
29. Z. Zhiqiang Ma, J. Lu, X. Wang, C. Chen, Chem. Commun. 2011, 47, 427-429.
30. H. Hoffmann, T. Lindel, Synthesis 2003, 12, 1753-1783
31. A. Al Mourabit, P. Potier, Eur. J. Org. Chem. 2001, 237-243
32. M. Köck, A. Grube, I. B. Seiple, P. S. Baran, Angew. Chem. 2007, 119, 6706-6714
33. Angew. Chem. Int. Ed. 2007, 46, 6586-6594
34. A. Al-Mourabit, M. Zancanella, S. Tilvi, D. Romo, Nat. Prod. Rep. 2011, 28, 1229-1260.
35. For a bioinspired strategy to phakellin, see
36. L. H. Foley, G. Büechi, J. Am. Chem. Soc. 1982, 104, 1776-1777. For bioinspired approaches to palau'amine and related PAIs, see
37. A. S. Dilley, D. Romo, Org. Lett. 2001, 3, 1535-1538
38. S. G. Koenig, S. M. Miller, K. A. Leonard, R. S. Lowe, B. C. Chen, D. J. Austin, Org. Lett. 2003, 5, 2203-2206
39. Q. Li, P. Hurley, H. Ding, A. G. Roberts, R. Akella, P. G. Harran, J. Org. Chem. 2009, 74, 5909-5919.
40. M. Köck, M. Z. Assmann, Z. Naturforsch. C 2002, 57, 157-160
41. P. A. Keifer, R. E. Schwartz, M. E. S. Koker, R. G. Hughes, Jr., D. Rittschof, K. L. Rinehart, J. Org. Chem. 1991, 56, 2965-2975.
42. P. Bélanger, Tetrahedron Lett. 1979, 20, 2505-2508.
43. D. S. Dalisay, B. I. Morinaka, C. K. Skepper, T. F. Molinski, J. Am. Chem. Soc. 2009, 131, 7552-7553.
44. Baran and co-workers propose that 1a is biosynthetically transformed into the isomeric ageliferin by thermal cyclobutane ring opening of 1a into a diradical which re-closes to the cyclohexene, see:, B. H. Northrop, D. P. O'Malley, A. L. Zografos, P. S. Baran, K. N. Houk, Angew. Chem. 2006, 118, 4232-4236
45. Angew. Chem. Int. Ed. 2006, 45, 4126-4130. Al-Mourabit and co-workers favor an alternative even-electron pathway from 3b to 4b. See Ref. [9].
46. T. Endo, M. Tsuda, T. Okada, S. Mitsuhashi, H. Shima, K. Kikuchi, Y. Mikami, J. Fromont, J. Kobayashi, J. Nat. Prod. 2004, 67, 1262-1267.
47. Peroxidase-promoted radical pairings generate Ci-C bonds without incorporation of oxygen
48. T. M. Kutchan, W. M. Chou, Plant J. 1998, 15, 289-300
49. K. A. Nielsen, B. L. Lindberg-Møller, in Cytochrome P450 (Ed.:, P. R. Ortiz de Montellano,), Kluwer, Dordrecht, 2005, pp. 553-574.
50. There is no a priori reason to assume the involvement of radical cation intermediates over radical anions except for abundant precedence of peroxidases in Ci-C coupling reactions, relatively low oxidation potential of vinyl-2-aminoimidazoles, and the experimental evidence presented herein. An efficient photochemical catalytic redox-neutral synthesis of cyclobutanes by radical anion coupling has been demonstrated., J. Du, T. P. Yoon, J. Am. Chem. Soc. 2009, 131, 14604-14605.
51. W. Bao, D. M. O'Malley, R. R. Sederoff, Science 1993, 260, 672-674. We thank an anonymous reviewer for this analogy.
52. G. Sharma, B. Magdoff-Fairchild, J. Org. Chem. 1977, 42, 4118-4124
53. G. de Nanteuil, A. Ahond, J. Guilhem, C. Poupat, E. Tran Huu Dau, P. Potier, M. Pusset, J. Pusset, P. Laboute, Tetrahedron 1985, 41, 6019-6033.
54. L. B. Davin, H.-B. Wang, A. L. Crowell, D. L. Bedgar, D. M. Martin, S. Sarkanen, N. G. Lewis, Science 1997, 275, 362-366.