Total synthesis of macbecin I

Angewandte Chemie - International Edition

Volumn 47, Issue 21, 2008, Pages 4005-4008

  Belardi, Justin K ^a   Micalizio, Glenn C ^a  

^a YALE UNIVERSITY   (United States)

Author keywords

Ansamycin antibiotics; Cross coupling; Natural products; Titanium; Total synthesis

Indexed keywords

ACETYLENE; ALDEHYDES; BIOCHEMICAL ENGINEERING; BIOCHEMISTRY; COMPLEXATION; ORGANIC COMPOUNDS; SYNTHESIS (CHEMICAL); TITANIUM;

ANSAMYCIN ANTIBIOTICS; CROSS-COUPLING; NATURAL PRODUCTS; TOTAL SYNTHESIS;

TITANIUM COMPOUNDS;

BENZOQUINONE DERIVATIVE; MACBECIN I; MACROCYCLIC LACTAM;

ARTICLE; CHEMISTRY; CONFORMATION; STEREOISOMERISM; SYNTHESIS;

BENZOQUINONES; LACTAMS, MACROCYCLIC; MOLECULAR CONFORMATION; STEREOISOMERISM;

EID: 47049110496     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200800400     Document Type: Article

References (54)

1. For recent reviews on the biological activity of benzoquinone ansamycins, see: a)W. Xu, L. Neckers, Clin. Cancer Res. 2007, 13, 1625-1629;
2. b) Y. Miyata, Curr. Pharm. Des. 2005, 11, 1131-1138.
3. For total syntheses of benzoquinone ansamycins, see: macbecin I: a) R. Baker, J. L. Castro, J. Chem. Soc. Chem. Commun. 1989, 378-381;
4. b) R. Baker, J. L. Castro, J. Chem. Soc. Perkin Trans. 1 1990, 47-65;
5. c) D. A. Evans, S. J. Miller, M. D. Ennis, P. L. Ornstein, J. Org. Chem. 1992, 57, 1067-1069;
6. d) D. A. Evans, S. J. Miller, M. D. Ennis, J. Org. Chem. 1993, 58, 471-485;
7. e) J. S. Panek, F. Xu, J. Am. Chem. Soc. 1995, 117, 10587-10588;
8. f) J. S. Panek, F. Xu, A. C. RondGn, J. Am. Chem. Soc. 1998, 120, 4113-4122;
9. herbimycin A: g) M. Nakata, T. Osumi, A. Ueno, T. Kimura, T. Tamai, K. Tatsuta, Tetrahedron Lett. 1991, 32, 6015-6018;
10. h) K. D. Carter, J. S. Panek, Org. Lett. 2004, 6, 55-57;
11. i) S. Canova, V. Bellosta, A. Bigot, P. Mailliet, S. Mignani, J. Cossy, Org. Lett. 2007, 9, 145-148;
12. geldanamycin: j) M. B. Andrus, E. L. Meredith, B. L. Simmons, B. B. V. Soma Sekhar, E. J. Hicken, Org. Lett. 2002, 4, 3549-3552;
13. k) M. B. Andrus, E. L. Meredith, E. J. Hicken, B. L. Simmons, R. R. Glancey, W. Ma, J. Org. Chem. 2003, 68, 8162-8169;
14. for formal total syntheses of macbecin I, see: l) S. J. Coutts, J. Kallmerten, Tetrahedron Lett. 1990, 31, 4305-4308;
15. m) S. F. Martin, J. A. Dodge, L. E. Burgess, M. Hartmann, J. Org. Chem. 1992, 57, 1070-1072;
16. n) S. F. Martin, J. A. Dodge, L. E. Burgess, C. Limberakis, M. Hartmann, Tetrahedron 1996, 52, 3229-3246; for a formal total synthesis of herbimycin A, see reference [2n].
17. L. Whitesell, E. G. Mimnaugh, B. De Costa, C. E. Myers, L. M. Neckers, Proc. Natl. Acad. Sci. Usa 1994, 91, 8324-8328.
18. For studies on synthetic derivatives of the benzoquinone ansamycins, see: a) S. D. Kuduk, F. F. Zheng, L. Sepp-Lorenzino, N. Rosen, S. J. Danishefsky, Bioorg. Med. Chem. Lett. 1999, 9, 1233-1238;
19. b) T. Bach, A. Lemarchand, Synlett 2002, 1302-1304;
20. c) A. Lemarchand, T. Bach, Tetrahedron 2004, 60, 9659-9673;
21. d) R. C. Clevenger, B. S. S. Blagg, Org. Lett. 2004, 6, 4459-4462;
22. e) J.-Y. Le Brazidec, A. Kamal, D. Busch, L. Thao, L. Zhang, G. Timony, R. Grecko, K. Trent, R. Lough, T. Salazar, S. Khan, F. Burrows, M. F. Boehm, J. Med. Chem. 2004, 47, 3865-3873;
23. f) Z.-Q. Tian, Y. Liu, D. Zhang, Z. Wang, S. D. Dong, C. W. Carreras, Y. Zhow, G. Rastelli, D. V. Santi, D. C. Myles, Bioorg. Med. Chem. 2004, 12, 5317-5329;
24. g) A. Lemarchand, T. Bach, Synthesis 2005, 1977-1990;
25. h) H. Cheng, X. Cao, M. Xian, L. Fang, T. B. Cai, J. J. Ji, J. B. Tunac, D. Sun, D. P. G. Wang, J. Med. Chem. 2005, 48, 645-652;
26. i) G. Shen, M. Wang, T. R. Welch, B. S. J. Blagg, J. Org. Chem. 2006, 71, 7618-7631;
27. j) G. Chiosis, J. Aguirre, C. V. Nicchitta, Bioorg. Med. Chem. Lett. 2006, 16, 3529-3532;
28. k) J. Ge, E. Normant, J. R. Porter, J. A. Ali, M. S. Dembski, Y. Gao, A. T. Georges, L. Grenier, R. H. Pak, J. Patterson, J. R. Sydor, T. T. Tibbitts, J. K. Tong, J. Adams, V. J. Palombella, J. Med. Chem. 2006, 49, 4606-4615;
29. l) C. S. P. McErlean, N. Proisy, C. J. Davis, N. A. Boland, S. Y. Sharp, K. Boxall, A. M. Z. Slawin, P. Workman, C. J. Moody, Org. Biomol. Chem. 2007, 5, 531-546.
30. P. A. Wender, B. L. Miller in Organic Synthesis: Theory and Applications, Vol. 2 (Ed.: T. Hudlicky), JAI, Greenwich, 1993, pp. 27-66.
31. For an early example of a titanium-mediated coupling of an alkyne with an aldehyde, see: a) F. Sato, H. Kanbara, Y. Tanaka, Tetrahedron Lett. 1984, 25, 5063-5066;
32. for an early example of a titanium alkoxide mediated coupling of an internal alkyne with an aldehyde, see: b) K. Harada, H. Urabe, F. Sato, Tetrahedron Lett. 1995, 36, 3203-3206;
33. for examples of the alkoxide-directed titanium-mediated coupling of internal alkynes with aldehydes for polyketide synthesis, see: c) A. B. Bahadoor, A. Flyer, G. C. Micalizio, J. Am. Chem. Soc. 2005, 127, 3694-3695;
34. d) A. B. Bahadoor, G. C. Micalizio, Org. Lett. 2006, 8, 1181-1184;
35. e) L. J. Perez, G. C. Micalizio, Synthesis 2008, 627-648;
36. for a review of the chemistry of titanium alkoxides, see: f) O. G. Kulinkovich, A. de Meijere, Chem. Rev. 2000, 100, 2789-2834;
37. g) F. Sato, H. Urabe, S. Okamoto, Chem. Rev. 2000, 100, 2835-2886;
38. h) Titanium and Zirconium in Organic Synthesis (Ed.: I. Marek), Wiley-VCH, Weinheim, 2002, p. 512;
39. for applications of titanium alkoxide mediated C-C bond formation in total synthesis, see: i) S. Okamoto, K. Subburaj, F. Sato, J. Am. Chem. Soc. 2000, 122, 11244-11245;
40. j) L. R. Reddy, J.-F. Fournier, B. V. Subba Reddy, E. J. Corey, Org. Lett. 2005, 7, 2699-2701;
41. k) G. W. O'Niel, A. J. Phillips, J. Am. Chem. Soc. 2006, 128, 5340-5341;
42. l) K. A. Keaton, A. J. Phillips, J. Am. Chem. Soc. 2006, 128, 408-409.
43. A. G. Myers, B. H. Yang, H. Chen, L. McKinstry, D. J. Kopecky, J. L. Gleason, J. Am. Chem. Soc. 1997, 119, 6496-6511.
44. a) J. A. Marshall, Chem. Rev. 1996, 96, 31-47;
45. b) J. A. Marshall, X. Wang, J. Org. Chem. 1992, 57, 1242-1252;
46. for the synthesis of allenyl stannanes, see: c) J. A. Marshall, H. Chobanian, Org. Synth. 2005, 82, 43-54.
47. a) J. A. Marshall, C. M. Grant, J. Org. Chem. 1999, 64, 8214-8219;
48. b) J. A. Marshall, B. A. Johns, J. Org. Chem. 2000, 65, 1501-1510;
49. c) J. A. Marshall, H. R. Chobanian, M. M. Yanik, Org. Lett. 2001, 3, 3369-3372.
50. a) K. Sonogashira, Y. Tohda, N. Hagihara, Tetrahedron Lett. 1975, 16, 4467-4470;
51. b) K. Sonogashira, J. Organomet. Chem. 2002, 653, 46-49.
52. X. Li, X. Zeng, Tetrahedron Lett. 2006, 47, 6839-6842.
53. G. Saha, M. K. Basu, S. Kim, Y.-J. Jung, Y. Adiyaman, M. Adiyaman, W. S. Powell, G. A. FitzGerald, J. Rokach, Tetrahedron Lett. 1999, 40, 7179-7183.
54. See the Supporting Information for additional information.