Total synthesis of (+)-concanamycin F

Angewandte Chemie - International Edition

Volumn 39, Issue 7, 2000, Pages 1308-1312

  Paterson, Ian ^a   Doughty, Victoria A ^a   McLeod, Malcolm D ^a   Trieselmann, Thomas ^a  

^a UNIVERSITY OF CAMBRIDGE   (United Kingdom)

Author keywords

Aldol reactions; Boron; Macrolides; Natural products; Total synthesis

Indexed keywords

CONCANAMYCIN F; MACROLIDE; NATURAL PRODUCT; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CYCLIZATION; POLYMERIZATION; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0034599684     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(20000403)39:7<1308::AID-ANIE1308>3.0.CO;2-7     Document Type: Article

References (50)

1. a) H. Kinashi, K. Someno, K. Sakaguchi, T. Higashijima.T. Miyazawa, Tetrahedron Lett. 1981, 22, 3857;
2. H. Kinashi, K. Someno, K. Sakaguchi, T. Higashijima, T. Miyazawa, Tetrahedron Lett. 1981, 3861;
3. b) H. Kinashi, K. Sakaguchi, T. Higashijima, T. Miyazawa, J. Antibiot. 1982, 35, 1618;
4. c) H. Kinashi, K. Someno, K. Sakaguchi, J. Antibiot. 1984, 37, 1333;
5. d) J. W. Westley, C.-M. Liu, L. H. Sello, R. H. Evans, N. Troupe, J. F. Blount, A.M. Chiu, L. J. Torado, P. A. Miller, J. Antibiot. 1984, 37, 1738;
6. e) J.-T. Woo, C. Shinohara, K. Sakai, K. Hasumi, A. Endo, J. Antibiot. 1992, 45, 1108;
7. f) K. U. Bindseil, A. Zeeck, J. Org. Chem. 1993, 58, 5487.
8. a) E. J. Bowman, A. Siebers, K. Altendorf, Proc. Natl. Acad. Sci. USA 1988, 85, 7972;
9. b) Z. Vanek, J. Mateju, E. Curdova, Folia Microbiol (Prague) 1991, 36, 99;
10. c) S. Dröse, K. U. Bindseil, E. J. Bowman, A. Siebers, A. Zeeck, K. Altendorf, Biochemistry 1993, 32, 3902.
11. a) R. Guinea, L. Carrasco, Biochem. Biophys. Res. Commun. 1994, 201, 1270;
12. b) T. Kataoka, N. Shinohara, H. Takayama, K. Takaku, S. Kondo, S. Yonehara, K. Nagai, J. Immunol. 1996, 156, 3678;
13. c) N. Allan, Y. Chen, M. Schindler, S. M. Simon, J. Exp. Med. 1998, 187, 1583;
14. d) J.-T. Woo, Y. Ohba, K. Tagami, K. Sumitani, K. Yamaguchi, T. Tsuji, Biol. Pharm. Bull. 1996, 19, 297;
15. e) S. Gagliardi, G. Nadler, E. Consolandi, C. Parini, M. Morvan, M. N. Legave, P. Belfiore, A. Zocchetti, G. D. Clarke, I. James, P. Nambi, M. Gowen, C. Farina, J. Med. Chem. 1998, 41, 1568.
16. a) T. Jyojima, M. Katohno, N. Miyamoto, M. Nakata, S. Matsumura, K. Toshima, Tetrahedron Lett. 1998, 39, 6003;
17. b)T. Jyojima, N. Miyamoto, M. Katohno, M. Nakata, S. Matsumura, K. Toshima, Tetrahedron Lett. 1998, 39, 6007.
18. a) D. A. Evans, M. A. Caller, Tetrahedron Lett. 1993, 34, 6871;
19. b) K. Toshima, T. Jyojima, H. Yamaguchi, Y. Noguchi, T. Yoshida, H. Murase, M. Nakata, S. Matsumura, J. Org. Chem. 1997, 62, 3271;
20. c) K. A. Scheidt, A. Tasaka, T. D. Bannister, M. D. Wendt, W. R. Roush, Angew. Chem. 1999, 111, 1760;
21. Angew. Chem. Int. Ed. 1999, 38, 1652;
22. d) K. Makino, N. Nakajima, S. Hashimoto, O. Yonemitsu, Tetrahedron Lett. 1996, 37, 9077.
23. For previous synthetic studies, sec: a) I. Paterson, M. D. McLeod, Tetrahedron Lett. 1995, 36, 9065;
24. b) I. Paterson, M. D. McLeod, Tetrahedron Lett. 1997, 38, 4183.
25. a) I. Paterson, J. M. Goodman, M. Isaka, Tetrahedron Lett. 1989, 30, 7121;
26. b) I. Paterson, R. D. Norcross, R. A. Ward, P. Romea, M. A. Lister, J. Am. Chem. Soc. 1994, 116, 11287;
27. c) I. Paterson, D. J. Wallace, C. J. Cowden, Synthesis 1998, 639;
28. d) for a review of asymmetric aldol reactions using boron enolates, see: C. J. Cowden, I. Paterson, Org. React. 1997, 51, 1.
29. 1 side chain was used in the recent synthesis reported by the Roush group, see ref. [5c].
30. D. A. Evans, A. H. Hoveyda, J. Am. Chem. Soc. 1990, 112, 6447.
31. 2) 20°C, 2 h; 3) W-2 Raney Ni, H2, EtOH, 20°C, 30 min.
32. K. Takai, K. Nitta, K. Utimoto, J. Am. Chem. Soc. 1986, 108, 7408.
33. a) S. Ohira, Synth. Commun. 1989, 19, 561;
34. b) S. Müller, B. Liepold, G. J. Roth, H. J. Bestmann, Synlett 1990, 521.
35. H. X. Zhang, F. Guibe, G. Balavoine, J. Org. Chem. 1990, 55, 1857.
36. a) G. D. Allred, L. S. Liebeskind, J. Am. Chem. Soc. 1996, 118, 2748;
37. b) I. Paterson, J. Man, Tetrahedron Lett. 1997, 38, 695;
38. c) I. Paterson, H.-G. Lombart, C. Allerton, Org. Lett. 1999, 1, 19.
39. 4] and CuI gave 19 in low yield (20%).
40. a) E. D. Laganis, B. L. Chenard, Tetrahedron Lett. 1984, 25, 5831;
41. b) S. S. Bhagwat, P. R. Hamann, W. C. Still, J. Am. Chem. Soc. 1985, 107, 6372.
42. a) J. Inanaga, K. Hirata, H. Saeki, T. Katsuki, M. Yamaguchi, Bull. Chem. Soc. Jpn. 1979, 52, 1989;
43. b) M. Hikota, Y. Sakurai, K. Horita, O. Yonemitsu, Tetrahedron Lett. 1990, 31, 6367.
44. 2) retaining the silylene protecting group was prepared, but the macrocyclization failed under both Stille and Liebeskind coupling conditions.
45. a) V. Farina, B. Krishnan, J. Am. Chem. Soc. 1991, 113, 9585;
46. b) M. A. J. Duncton, G. Pattenden, J. Chem. Soc. Perkin Trans. I 1999, 1235.
47. S. V. Ley, J. Norman, W. P. Griffith, S. P. Marsden, Synthesis 1994, 639.
48. This aldol fragment coupling strategy was conceived based on our earlier work on swinholide A and scytophycin C, see: I. Paterson, J. G. Cumming, J. D. Smith, R. A. Ward, K.-S. Yeung, Tetrahedron Lett. 1994, 35, 3405.
49. 23 (ca. 3:1). For other related studies, see ref. [5c] and D. A. Evans, M. J. Dart, J. L. Duffy, M. G. Yang, J. Am. Chem. Soc. 1996, 118, 4322.
50. In contrast to its successful use with bafilomycin A, prolonged treatment of 24 or 25 with this reagent under the Roush conditions failed to deprotect the two TES ethers without decomposition, see K. A. Scheidt, H. Chen, B. C. Follows, S. R. Chemler, D. S. Coffey, W. R. Roush, J. Org. Chem. 1998, 63, 6436.