Applications of size-selective macrolactonizations to the synthesis of benzolactone-enamide core structures

Synthesis

Volumn , Issue 6, 2003, Pages 940-955

  Petri, Andreas F ^a   Kühnert, Sven M ^a   Scheufler, Frank ^a   Maier, Martin E ^a  

^a UNIVERSITY OF TÜBINGEN   (Germany)

Author keywords

Alkynes; Epoxides; Hydrostannations; Macrocycles; Ring closure; Stille reaction

Indexed keywords

CARBOXYLIC ACIDS; DERIVATIVES; REACTION KINETICS;

MACROLACTONIZATION;

SYNTHESIS (CHEMICAL);

2 [4,11 BIS(BENZYLOXY) 6,8 DIHYDROXY 1 UNDECENYL] 6 METHOXYBENZOIC ACID; 2 [7,8 DIHYDROXY 10 [(4 METHOXYBENZYL)OXY]DEC 1 ENYL] 6 METHOXYBENZOIC ACID; 2 [7,8 DIHYDROXY 9 [(4 METHOXYBENZYL)OXY]NON 1 ENYL] 6 METHOXYBENZOIC ACID; 7 (BENZYLOXY) 3 [3 (BENZYLOXY)PROPYL] 5 HYDROXY 14 METHOXY 3,4,5,6,7,8 HEXAHYDRO 1H 2 BENZOXACYCLODODECIN 1 ONE; AMIDE; BENZOIC ACID DERIVATIVE; BENZOLACTONE; ENAMIDE; HYDROXYL GROUP; LACTONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; CHEMICAL STRUCTURE; INFRARED RADIATION; MACROLACTONIZATION; PARTICLE SIZE; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY;

EID: 0038367701     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-38675     Document Type: Article

References (67)

1. Recent Reviews: (a) Yet, L. Chem. Rev. 2000, 100, 2963. (b) Maier, M. E. Angew. Chem. Int. Ed. 2000, 39, 2073; Angew. Chem. 2000, 112, 2153. (c) Fürstner, A. Synlett 1999, 1523.
2. Recent Reviews: (a) Yet, L. Chem. Rev. 2000, 100, 2963. (b) Maier, M. E. Angew. Chem. Int. Ed. 2000, 39, 2073; Angew. Chem. 2000, 112, 2153. (c) Fürstner, A. Synlett 1999, 1523.
3. Recent Reviews: (a) Yet, L. Chem. Rev. 2000, 100, 2963. (b) Maier, M. E. Angew. Chem. Int. Ed. 2000, 39, 2073; Angew. Chem. 2000, 112, 2153. (c) Fürstner, A. Synlett 1999, 1523.
4. Recent Reviews: (a) Yet, L. Chem. Rev. 2000, 100, 2963. (b) Maier, M. E. Angew. Chem. Int. Ed. 2000, 39, 2073; Angew. Chem. 2000, 112, 2153. (c) Fürstner, A. Synlett 1999, 1523.
5. See for example: Wiberg, K. B.; Waldron, R. F.; Schulte, G.; Saunders, M. J. Am. Chem. Soc. 1991, 113, 971.
6. Illuminati, G.; Mandolini, L. Acc. Chem. Res. 1981, 14, 95.
7. Baldwin, J. E. J. Chem. Soc., Chem. Commun. 1976, 734.
8. Mulzer, J.; Kirstein, H. M.; Buschmann, J.; Lehmann, C.; Luger, P. J. Am. Chem. Soc. 1990, 113, 910.
9. Hanessian, S.; Ma, J.; Wang, W. J. Am. Chem. Soc. 2001, 123, 10200.
10. Kageyama, M.; Tamura, T.; Nantz, M. H.; Roberts, J. C.; Somfai, P.; Whritenour, D. C.; Masamune, S. J. Am. Chem. Soc. 1990, 112, 7407.
11. Schuppan, J.; Wehlan, H.; Keiper, S.; Koert, U. Angew. Chem. Int. Ed. 2001, 40, 2063; Angew. Chem. 2001, 113, 2125.
12. Schuppan, J.; Wehlan, H.; Keiper, S.; Koert, U. Angew. Chem. Int. Ed. 2001, 40, 2063; Angew. Chem. 2001, 113, 2125.
13. White, J. D.; Blakemore, P. R.; Browder, C. C.; Hong, J.; Lincoln, C. M.; Nagornyy, P. A.; Robarge, L. A.; Wardrop, D. J. J. Am. Chem. Soc. 2001, 123, 8593.
14. For a review see: Yeung, K.-S.; Paterson, I. Angew. Chem. Int. Ed. 2002, 41, 4632; Angew. Chem. 2002, 114, 4826.
15. For a review see: Yeung, K.-S.; Paterson, I. Angew. Chem. Int. Ed. 2002, 41, 4632; Angew. Chem. 2002, 114, 4826.
16. Boyd, M. R.; Farina, C.; Belfiore, P.; Gagliardi, S.; Kim, J. W.; Hayakawa, Y.; Beutler, J. A.; McKee, T. C.; Bowman, B. J.; Bowman, E. J. J. Pharmacol. Exp. Ther. 2001, 291, 114.
17. Erickson, K. L.; Beutler, J. A.; Cardellina, J. H. II.; Boyd, M. R. J. Org. Chem. 1997, 62, 8188.
18. (a) Kunze, B.; Jansen, R.; Sasse, F.; Höfle, G.; Reichenbach, H. J. Antibiot. 1998, 51, 1075.
19. (b) Jansen, R.; Kunze, B.; Reichenbach, H.; Höfle, G. Eur. J. Org. Chem. 2000, 913.
20. Kim, J. W.; Shin-ya, K.; Furihata, K.; Hayakawa, Y.; Seto, H. J. Org. Chem. 1999, 64, 153.
21. Dekker, K. A.; Aiello, R. J.; Hirai, H.; Inagaki, T.; Sakakibara, T.; Suzuki, Y.; Thompson, J. F.; Yamauchi, Y.; Kojima, N. J. Antibiot. 1998, 51, 14.
22. Total syntheses of salicylihalamide: (a) Wu, Y.; Esser, L.; De Brabander, J. K. Angew. Chem. Int. Ed. 2000, 39, 4308; Angew. Chem. 2000, 112, 4478. (b) Labrecque, D.; Charron, S.; Rej, R.; Blais, C.; Lamothe, S. Tetrahedron Lett. 2001, 42, 2645. (c) Smith, A. B. III; Zheng, J. Synlett 2001, 1019. (d) Snider, B. B.; Song, F. Org. Lett. 2001, 3, 1817. (e) Fürstner, A.; Dierkes, T.; Thiel, O.; Blanda, G. Chem.-Eur. J. 2001, 7, 5286. (f) Wu, Y.; Liao, X.; Wang, R.; Xie, X.-S.; De Brabander, J. K. J. Am. Chem. Soc. 2002, 124, 3245. (g) Smith, A. B. III; Zheng, J. Tetrahedron 2002, 58, 6455.
23. Total syntheses of salicylihalamide: (a) Wu, Y.; Esser, L.; De Brabander, J. K. Angew. Chem. Int. Ed. 2000, 39, 4308; Angew. Chem. 2000, 112, 4478. (b) Labrecque, D.; Charron, S.; Rej, R.; Blais, C.; Lamothe, S. Tetrahedron Lett. 2001, 42, 2645. (c) Smith, A. B. III; Zheng, J. Synlett 2001, 1019. (d) Snider, B. B.; Song, F. Org. Lett. 2001, 3, 1817. (e) Fürstner, A.; Dierkes, T.; Thiel, O.; Blanda, G. Chem.-Eur. J. 2001, 7, 5286. (f) Wu, Y.; Liao, X.; Wang, R.; Xie, X.-S.; De Brabander, J. K. J. Am. Chem. Soc. 2002, 124, 3245. (g) Smith, A. B. III; Zheng, J. Tetrahedron 2002, 58, 6455.
24. Total syntheses of salicylihalamide: (a) Wu, Y.; Esser, L.; De Brabander, J. K. Angew. Chem. Int. Ed. 2000, 39, 4308; Angew. Chem. 2000, 112, 4478. (b) Labrecque, D.; Charron, S.; Rej, R.; Blais, C.; Lamothe, S. Tetrahedron Lett. 2001, 42, 2645. (c) Smith, A. B. III; Zheng, J. Synlett 2001, 1019. (d) Snider, B. B.; Song, F. Org. Lett. 2001, 3, 1817. (e) Fürstner, A.; Dierkes, T.; Thiel, O.; Blanda, G. Chem.-Eur. J. 2001, 7, 5286. (f) Wu, Y.; Liao, X.; Wang, R.; Xie, X.-S.; De Brabander, J. K. J. Am. Chem. Soc. 2002, 124, 3245. (g) Smith, A. B. III; Zheng, J. Tetrahedron 2002, 58, 6455.
25. Total syntheses of salicylihalamide: (a) Wu, Y.; Esser, L.; De Brabander, J. K. Angew. Chem. Int. Ed. 2000, 39, 4308; Angew. Chem. 2000, 112, 4478. (b) Labrecque, D.; Charron, S.; Rej, R.; Blais, C.; Lamothe, S. Tetrahedron Lett. 2001, 42, 2645. (c) Smith, A. B. III; Zheng, J. Synlett 2001, 1019. (d) Snider, B. B.; Song, F. Org. Lett. 2001, 3, 1817. (e) Fürstner, A.; Dierkes, T.; Thiel, O.; Blanda, G. Chem.-Eur. J. 2001, 7, 5286. (f) Wu, Y.; Liao, X.; Wang, R.; Xie, X.-S.; De Brabander, J. K. J. Am. Chem. Soc. 2002, 124, 3245. (g) Smith, A. B. III; Zheng, J. Tetrahedron 2002, 58, 6455.
26. Total syntheses of salicylihalamide: (a) Wu, Y.; Esser, L.; De Brabander, J. K. Angew. Chem. Int. Ed. 2000, 39, 4308; Angew. Chem. 2000, 112, 4478. (b) Labrecque, D.; Charron, S.; Rej, R.; Blais, C.; Lamothe, S. Tetrahedron Lett. 2001, 42, 2645. (c) Smith, A. B. III; Zheng, J. Synlett 2001, 1019. (d) Snider, B. B.; Song, F. Org. Lett. 2001, 3, 1817. (e) Fürstner, A.; Dierkes, T.; Thiel, O.; Blanda, G. Chem.-Eur. J. 2001, 7, 5286. (f) Wu, Y.; Liao, X.; Wang, R.; Xie, X.-S.; De Brabander, J. K. J. Am. Chem. Soc. 2002, 124, 3245. (g) Smith, A. B. III; Zheng, J. Tetrahedron 2002, 58, 6455.
27. Total syntheses of salicylihalamide: (a) Wu, Y.; Esser, L.; De Brabander, J. K. Angew. Chem. Int. Ed. 2000, 39, 4308; Angew. Chem. 2000, 112, 4478. (b) Labrecque, D.; Charron, S.; Rej, R.; Blais, C.; Lamothe, S. Tetrahedron Lett. 2001, 42, 2645. (c) Smith, A. B. III; Zheng, J. Synlett 2001, 1019. (d) Snider, B. B.; Song, F. Org. Lett. 2001, 3, 1817. (e) Fürstner, A.; Dierkes, T.; Thiel, O.; Blanda, G. Chem.-Eur. J. 2001, 7, 5286. (f) Wu, Y.; Liao, X.; Wang, R.; Xie, X.-S.; De Brabander, J. K. J. Am. Chem. Soc. 2002, 124, 3245. (g) Smith, A. B. III; Zheng, J. Tetrahedron 2002, 58, 6455.
28. Total syntheses of salicylihalamide: (a) Wu, Y.; Esser, L.; De Brabander, J. K. Angew. Chem. Int. Ed. 2000, 39, 4308; Angew. Chem. 2000, 112, 4478. (b) Labrecque, D.; Charron, S.; Rej, R.; Blais, C.; Lamothe, S. Tetrahedron Lett. 2001, 42, 2645. (c) Smith, A. B. III; Zheng, J. Synlett 2001, 1019. (d) Snider, B. B.; Song, F. Org. Lett. 2001, 3, 1817. (e) Fürstner, A.; Dierkes, T.; Thiel, O.; Blanda, G. Chem.-Eur. J. 2001, 7, 5286. (f) Wu, Y.; Liao, X.; Wang, R.; Xie, X.-S.; De Brabander, J. K. J. Am. Chem. Soc. 2002, 124, 3245. (g) Smith, A. B. III; Zheng, J. Tetrahedron 2002, 58, 6455.
29. Total syntheses of salicylihalamide: (a) Wu, Y.; Esser, L.; De Brabander, J. K. Angew. Chem. Int. Ed. 2000, 39, 4308; Angew. Chem. 2000, 112, 4478. (b) Labrecque, D.; Charron, S.; Rej, R.; Blais, C.; Lamothe, S. Tetrahedron Lett. 2001, 42, 2645. (c) Smith, A. B. III; Zheng, J. Synlett 2001, 1019. (d) Snider, B. B.; Song, F. Org. Lett. 2001, 3, 1817. (e) Fürstner, A.; Dierkes, T.; Thiel, O.; Blanda, G. Chem.-Eur. J. 2001, 7, 5286. (f) Wu, Y.; Liao, X.; Wang, R.; Xie, X.-S.; De Brabander, J. K. J. Am. Chem. Soc. 2002, 124, 3245. (g) Smith, A. B. III; Zheng, J. Tetrahedron 2002, 58, 6455.
30. Synthetic studies: (a) Fürstner, A.; Seidel, G.; Kindler, N. Tetrahedron 1999, 55, 8215. (b) Fürstner, A.; Thiel, O. R.; Blanda, G. Org. Lett. 2000, 2, 3731. (c) Feutrill, J. T.; Holloway, G. A.; Hilli, F.; Hügel, H. M.; Rizzacasa, M. A. Tetrahedron Lett. 2000, 41, 8569. (d) Georg, G. I.; Ahn, Y. M.; Blackman, B.; Farokhi, F.; Flaherty, P. T.; Mossman, C. J.; Roy, S.; Yang, K. Chem. Commun. 2001, 255. (e) Bauer, M.; Maier, M. E. Org. Lett. 2002, 4, 2205.
31. Synthetic studies: (a) Fürstner, A.; Seidel, G.; Kindler, N. Tetrahedron 1999, 55, 8215. (b) Fürstner, A.; Thiel, O. R.; Blanda, G. Org. Lett. 2000, 2, 3731. (c) Feutrill, J. T.; Holloway, G. A.; Hilli, F.; Hügel, H. M.; Rizzacasa, M. A. Tetrahedron Lett. 2000, 41, 8569. (d) Georg, G. I.; Ahn, Y. M.; Blackman, B.; Farokhi, F.; Flaherty, P. T.; Mossman, C. J.; Roy, S.; Yang, K. Chem. Commun. 2001, 255. (e) Bauer, M.; Maier, M. E. Org. Lett. 2002, 4, 2205.
32. Synthetic studies: (a) Fürstner, A.; Seidel, G.; Kindler, N. Tetrahedron 1999, 55, 8215. (b) Fürstner, A.; Thiel, O. R.; Blanda, G. Org. Lett. 2000, 2, 3731. (c) Feutrill, J. T.; Holloway, G. A.; Hilli, F.; Hügel, H. M.; Rizzacasa, M. A. Tetrahedron Lett. 2000, 41, 8569. (d) Georg, G. I.; Ahn, Y. M.; Blackman, B.; Farokhi, F.; Flaherty, P. T.; Mossman, C. J.; Roy, S.; Yang, K. Chem. Commun. 2001, 255. (e) Bauer, M.; Maier, M. E. Org. Lett. 2002, 4, 2205.
33. Synthetic studies: (a) Fürstner, A.; Seidel, G.; Kindler, N. Tetrahedron 1999, 55, 8215. (b) Fürstner, A.; Thiel, O. R.; Blanda, G. Org. Lett. 2000, 2, 3731. (c) Feutrill, J. T.; Holloway, G. A.; Hilli, F.; Hügel, H. M.; Rizzacasa, M. A. Tetrahedron Lett. 2000, 41, 8569. (d) Georg, G. I.; Ahn, Y. M.; Blackman, B.; Farokhi, F.; Flaherty, P. T.; Mossman, C. J.; Roy, S.; Yang, K. Chem. Commun. 2001, 255. (e) Bauer, M.; Maier, M. E. Org. Lett. 2002, 4, 2205.
34. Synthetic studies: (a) Fürstner, A.; Seidel, G.; Kindler, N. Tetrahedron 1999, 55, 8215. (b) Fürstner, A.; Thiel, O. R.; Blanda, G. Org. Lett. 2000, 2, 3731. (c) Feutrill, J. T.; Holloway, G. A.; Hilli, F.; Hügel, H. M.; Rizzacasa, M. A. Tetrahedron Lett. 2000, 41, 8569. (d) Georg, G. I.; Ahn, Y. M.; Blackman, B.; Farokhi, F.; Flaherty, P. T.; Mossman, C. J.; Roy, S.; Yang, K. Chem. Commun. 2001, 255. (e) Bauer, M.; Maier, M. E. Org. Lett. 2002, 4, 2205.
35. Total syntheses of apicularen A: (a) Bhattacharjee, A.; Seguil, O. R.; De Brabander, J. K. Tetrahedron Lett. 2001, 42, 1217. (b) Lewis, A.; Stefanuti, I.; Swain, S. A.; Smith, S. A.; Taylor, R. J. K. Tetrahedron Lett. 2001, 42, 5549. (c) Nicolaou, K. C.; Kim, D. W.; Baati, R. Angew. Chem. Int. Ed. 2002, 41, 3701; Angew. Chem. 2002, 114, 3853; (d) Lewis, A.; Stefanuti, I.; Swain, S. A.; Smith, S. A.; Taylor, R. J. K. Org. Bioml. Chem. 2003, 104.
36. Total syntheses of apicularen A: (a) Bhattacharjee, A.; Seguil, O. R.; De Brabander, J. K. Tetrahedron Lett. 2001, 42, 1217. (b) Lewis, A.; Stefanuti, I.; Swain, S. A.; Smith, S. A.; Taylor, R. J. K. Tetrahedron Lett. 2001, 42, 5549. (c) Nicolaou, K. C.; Kim, D. W.; Baati, R. Angew. Chem. Int. Ed. 2002, 41, 3701; Angew. Chem. 2002, 114, 3853; (d) Lewis, A.; Stefanuti, I.; Swain, S. A.; Smith, S. A.; Taylor, R. J. K. Org. Bioml. Chem. 2003, 104.
37. Total syntheses of apicularen A: (a) Bhattacharjee, A.; Seguil, O. R.; De Brabander, J. K. Tetrahedron Lett. 2001, 42, 1217. (b) Lewis, A.; Stefanuti, I.; Swain, S. A.; Smith, S. A.; Taylor, R. J. K. Tetrahedron Lett. 2001, 42, 5549. (c) Nicolaou, K. C.; Kim, D. W.; Baati, R. Angew. Chem. Int. Ed. 2002, 41, 3701; Angew. Chem. 2002, 114, 3853; (d) Lewis, A.; Stefanuti, I.; Swain, S. A.; Smith, S. A.; Taylor, R. J. K. Org. Bioml. Chem. 2003, 104.
38. Total syntheses of apicularen A: (a) Bhattacharjee, A.; Seguil, O. R.; De Brabander, J. K. Tetrahedron Lett. 2001, 42, 1217. (b) Lewis, A.; Stefanuti, I.; Swain, S. A.; Smith, S. A.; Taylor, R. J. K. Tetrahedron Lett. 2001, 42, 5549. (c) Nicolaou, K. C.; Kim, D. W.; Baati, R. Angew. Chem. Int. Ed. 2002, 41, 3701; Angew. Chem. 2002, 114, 3853; (d) Lewis, A.; Stefanuti, I.; Swain, S. A.; Smith, S. A.; Taylor, R. J. K. Org. Bioml. Chem. 2003, 104.
39. Total syntheses of apicularen A: (a) Bhattacharjee, A.; Seguil, O. R.; De Brabander, J. K. Tetrahedron Lett. 2001, 42, 1217. (b) Lewis, A.; Stefanuti, I.; Swain, S. A.; Smith, S. A.; Taylor, R. J. K. Tetrahedron Lett. 2001, 42, 5549. (c) Nicolaou, K. C.; Kim, D. W.; Baati, R. Angew. Chem. Int. Ed. 2002, 41, 3701; Angew. Chem. 2002, 114, 3853; (d) Lewis, A.; Stefanuti, I.; Swain, S. A.; Smith, S. A.; Taylor, R. J. K. Org. Bioml. Chem. 2003, 104.
40. Bhattacharjee, A.; De Brabander, J. K. Tetrahedron Lett. 2000, 41, 8069.
41. Scheufler, F.; Maier, M. E. Synlett 2001, 1221.
42. Harvey, D. F.; Lund, K. P.; Neil, D. A. J. Am. Chem. Soc. 1992, 114, 8424.
43. Review: Kolb, H. C.; VanNieuwenhze, M. S.; Sharpless, K. B. Chem. Rev. 1994, 94, 2483.
44. Zhang, H. X.; Guibé, F.; Balavoine, G. J. Org. Chem. 1990, 55, 1857.
45. Kühnert, S. M.; Maier, M. E. Org. Lett. 2002, 4, 643.
46. Inanaga, J.; Hirata, K.; Saeki, H.; Katsuki, T.; Yamaguchi, M. Bull. Chem. Soc. Jpn. 1979, 52, 1989.
47. Capon, R. J.; Barrow, R. A. J. Org. Chem. 1998, 63, 75.
48. Huang, H.; Forsyth, C. J. J. Org. Chem. 1997, 62, 8595.
49. (a) Ragoussis, N.; Ragoussis, V. J. Chem. Soc., Perkin Trans. 1 1998, 3529.
50. (b) Berkenbusch, T.; Brückner, R. Tetrahedron 1998, 54, 11471.
51. Casadei, M. A.; Galli, C.; Mandolini, L. J. Am. Chem. Soc. 1984, 104, 1051.
52. For a related transannular approach see: Hilli, F.; White, J., M.; Rizzacasa, M. A. Tetrahedron Lett. 2002, 43, 8507.
53. (a) Brunner, H.; Lautenschlager, H.-H. Synthesis 1989, 706.
54. (b) Berninger, J.; Koert, U.; Eisenberg-Höhl, C.; Knochel, P. Chem. Ber. 1995, 128, 1021.
55. Solladié, G.; Fernandez, I.; Maestro, C. Tetrahedron: Asymmetry 1991, 2, 801.
56. Smith, A. B. III; Lupo, A. T. Jr.; Ohba, M.; Chen, K. J. Am. Chem. Soc. 1989, 11, 6648.
57. Chen, K.-M.; Hardtmann, G. E.; Prasad, K.; Repic, O.; Shapiro, M. J. Tetrahedron Lett. 1987, 28, 155.
58. (a) Farina, V.; Krishnan, B. J. Am. Chem. Soc. 1991, 113, 9585.
59. (b) Farina, V.; Krishnamurthy, V.; Scott, W. J. Org. React. 1997, 50, 1.
60. (a) Smith, A. B. III; Boldi, A. M. J. Am. Chem. Soc. 1997, 119, 6925.
61. (b) Smith, A. B. III; Condon, S. M.; McCauley, J. A. Acc. Chem. Res. 1998, 31, 35.
62. (c) Smith, A. B. III; Pitram, S. M. Org. Lett. 1999, 1, 2001.
63. (d) Tietze, L. F.; Geissler, H.; Gewert, J. A.; Jakobi, U. Synlett 1994, 511.
64. Silverman, R. B.; Lu, X.; Banik, G. M. J. Org. Chem. 1992, 57, 6617.
65. (a) Furrow, M. E.; Schaus, S. E.; Jacobsen, E. N. J. Org. Chem. 1998, 63, 6776.
66. (b) Schaus, S. E.; Brandes, B. D.; Larrow, J. F.; Tokunaga, M.; Hansen, K. B.; Gould, A. E.; Furrow, M. E.; Jacobsen, E. N. J. Am. Chem. Soc. 2002, 124, 1307.
67. Yamaguchi, M.; Hirao, I. Tetrahedron Lett. 1983, 24, 391.