Intra- And intermolecular oxa-pictet-spengler cyclization strategy for the enantioselective synthesis of deoxy analogues of (+)-nanomycin A methyl ester, (+)-eleutherin, (+)-allo-eleutherin, and (+)-thysanone

European Journal of Organic Chemistry

Volumn , Issue 23, 2010, Pages 4442-4449

  Sawant, Rajiv T ^a   Jadhav, Satish G ^a   Waghmode, Suresh B ^a  

^a UNIVERSITY OF PUNE   (India)

Author keywords

Antibiotics; Cyclization; Enantioselectivity; Organocatalysis; Qui ones

Indexed keywords

EID: 77955391035     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.201000476     Document Type: Article

References (55)

1. For a reviews on isolation, structure, and synthesis of pyranonaphthoquinone antibiotics, see:
2. a) J. Sperry, P. Bachu, M. A. Brimble, Nat. Prod. Rep 2008, 25, 376-400;
3. b) M. A. Brimble, M. R. Nairn, H. Prabaharan, Tetrahedron 2000, 56, 1937-1992;
4. c) M. A. Brimble, M. R. Nairn, L. Duncalf, Nat. Prod. Rep. 1999, 16, 267-281.
5. a) S. Omura, H. Tanaka, Y. Koyama, R. Oiwa, M. Katagiri, T. Nagai, T Hâta, J. Antibiot. 1974, 27, 363-365;
6. b) H. Tanaka, Y. Koyama, J Awaya, H. Marumo, R. Oiwa, M.. Katagiri, T. Nagai, S. Omura, J. Antibiot. 1975, 28, 860-867.
7. a) G. A. Kraus, J. Shi, J. Org. Chem. 1990, 55, 1105-1106;
8. b) M. Yarnaguchi, S. Nakamura, T. Okuma, T. Minami, Tetrahedron Lett. 1990, 31, 3913-3916 and references cited therein.
9. a) T. Kometani, E. Yoshii, J. Chem. Soc. Perkin Trans. 1 1981, 1191-1196;
10. b) T. Kometani, E. Yoshii, J. Chem. Soc. Perkin Trans. 1 1981, 1197-1202;
11. c) U. P. Dhokte, A. S. Rao, Synth. Commun. 1988, 18, 597-605;
12. d) U. P. Dhokte, A. S. Rao, Synth. Commun. 1991,21, 1263-1271.
13. M. A. Brimble, P. Bachu, J. Sperry, Synthesis 2007, 18, 28872893.
14. H. Schmid, A. Ebnother, T. M. Meijer, Helv. Chim. Acta 1950, 33, 1751-1770.
15. a) H. Schmid, A. Ebnother, Helv. Chim. Acta 1951, 34, 561576;
16. b) H. Schmid, A. Ebnother, Helv. Chim. Acta 1951, 34, 1041-1049.
17. P. Krishnan, K. F. Bastow, Biochem. Pharmacol. 2000, 60, 1367-1379.
18. a) H. Schmid, W Eisenhuth, Helv. Chim. Acta 1958, 41, 20212041;
19. b) A. D. Webb, T. M. Harris, Tetrahedron Lett. 1977, 18, 2069-2071;
20. c) Y. Naruta, H. Uno, K. Maruyama, J. Chem. Soc, Chem. Commun. 1981, 1277-1278;
21. d) R. G. F. Giles, I. R. Green, V. I. Hugo, P. R. K. Mitchell, J. Chem. Soc, Chem.
22. Commun. 1983, 51-52;
23. e) R. G. F. Giles, I. R. Green, V. I. Hugo, S. C. Yorke, P. R. K. Mitchell, J Chem. Soc. Perkin Trans. 1 1984, 2383-2388;
24. f) G. A. Kraus, M. T. Molina, J. A. Walling, J. Chem. Soc, Chem. Commun. 1986, 1568-1569;
25. g) H. Uno, J. Org. Chem. 1986, 51, 350-358;
26. h) K. Kobayashi, M. Uchida, T. Uneda, M.. Tanmatsu, O. Morikawa, H. Konishi, Tetrahedron Lett. 1998, 39, 7725-7728.
27. a) L. M. Tewierik, C. Dimitriadis, C. D. Donner, M. Gill, B. Willems, Org. Biomol. Chem. 2006, 4, 3311-3318;
28. b) J. S. Gibson, O. Andrey, M. A. Brimble, Synthesis 2007, 2611-2613;
29. c) R. A. Fernandes, V. P. Chavan, A. B. Ingle, Tetrahedron Lett. 2008, 49, 6341-6343 and references cited therein.
30. P. Bachu, J Sperry, M. A. Brimble, Tetrahedron 2008, 64, 48274834.
31. S. B. Singh, M. G. Cordingley, R. G. Ball, J L. Smith, A. W. Dombrowski, M. A. Goetz, Tetrahedron Lett. 1991, 32, 52795282.
32. a) A. G. Kraus, H. Ogutu, Tetrahedron 2002, 58, 7391-7395;
33. b) V. J Bulbule, P. S. Koranne, V. H. Deshpan.de, H. B. Borate, Tetrahedron 2007, 63, 166-170 and references cited therein.
34. a) R. T. Sawant, S. B. Waghmode, Tetrahedron 2009, 65, 15991602;
35. b) R. T Sawant, S. B. Waghmode, Synth. Commun., DOI: 10.1080/ 00397910903221753;
36. c) R. T. Sawant, S. B. Waghmode, Tetrahedron 2010, 66, 2010-2014.
37. a) C. D. Donner, M. Gill, Tetrahedron Lett. 1999, 40, 39213924;
38. b) C. D. Donner, M. Gill, J. Chem. Soc. Perkin Trans. 1 2002, 938-948;
39. c) M. A. Brimble, R. J. R. Elliott, Tetrahedron 2002, 58, 183-189;
40. d) M. A. Brimble, S.I. Houghton, P.D. Woodgate, Tetrahedron 2007, 63, 880-887;
41. e) J. Sperry, M. A. Brimble, Synlett 2008, 12, 1910-1912;
42. f) J Sperry, T. Y. Yuen, M. A. Brimble, Synthesis 2009, 15, 2561-2569;
43. [11]and references cited therein.
44. For intramolecular oxa-Pictet-Spengler cyclization, see:
45. a) R. G. F. Giles, R. W Rickards, B. S. Senanayake, J. Chem. Soc Perkin Trans. 1 1997, 3361-3370;
46. b) R. G. F. Giles, R. W Rickards, B. S. Senanayake, J. Chem. Soc, Perkin Trans. 1 1998, 3949-3956;
47. c) D. A. Bianchi, F. Rua, T. S. Kaufman, Tetrahedron Lett. 2004, 45, 411-415;
48. d) R. G. F. Giles, J. D. McMamis, Tetrahedron Lett. 2009, 50, 6361-6363 and references cited. therein.
49. a) Y. Hayashi, J. Yamaguchi, K. Hibino, M. Shoji, Tetrahedron Lett. 2003, 44, 8293-8296;
50. b) G. Zhong, Angew. Chem. Int. Ed. 2003, 42, 4247-4250;
51. c) S. P. Brown, M. P. Brochu, C. J. Sinz, D.W. C MacMillan, J. Am. Chem. Soc, 2003, 125, 1080810809.
52. a) E. L. Larghi, T. S. Kaufmann, Synthesis 2006, 187-220;
53. b) B. Wunsch, M. Zoll, Liebigs Ann. Chem. 1992, 39-45.
54. A referee suggested, that the poor reactivity of bromide derivatives 13a and 20a towards Friedel-Crafts electrophilic cyclization is not due to the electron-withdrawing effect of bromine but due to the bulky bromine substituent at C-4 of the aryl ring, which requires the methyl group of the neighboring methoxy moiety to adopt such a conformation (out of plane) as to allow substitution of the unoccupied ortho position. This results in a decrease in the amount of conjugation with the aromatic ring, which therefore diminishes the activation of 13a and 20a towards Friedel-Crafts cyclization. At this stage we cannot exclude this possibility.
55. J. I. Retamal, V. M. Ruiz, R. A. Tapia, J. A. Valderrama, J. C. Vega, Synth. Commun. 1982, 12, 279-285.