Total syntheses of (-)-macrolactin a, (+)-macrolactin e, and (-)- macrolactinic acid: An exercise in stille cross-coupling chemistry

Journal of the American Chemical Society

Volumn 120, Issue 16, 1998, Pages 3935-3948

  Smith III, Amos B ^a   Ott, Gregory R ^a  

^a UNIVERSITY OF PENNSYLVANIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

MACROLACTIN A; MACROLACTIN E; MACROLACTINIC ACID; MACROLIDE; UNCLASSIFIED DRUG;

ANTIVIRAL ACTIVITY; ARTICLE; CHEMICAL MODIFICATION; CYCLIZATION; DRUG DESIGN; DRUG STRUCTURE; DRUG SYNTHESIS; FERMENTATION; STEREOCHEMISTRY;

EID: 0032577032     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja980203b     Document Type: Article

References (85)

1. Gustafson, K.; Roman, M.; Fenical, W. J. Am. Chem. Soc. 1989, 111, 7519.
2. Rychnovsky, S. D.; Skalitzky, D. J.; Pathirana, C.; Jensen, P. R.; Fenical, W. J. Am. Chem. Soc. 1992, 114, 671.
3. For a synthesis of 13,15-dimethoxymacrolactin A, which also exploits Stille and Suzuki cross-coupling chemistry for key bond constructions, see: Boyce, R. J.; Pattenden, G. Tetrahedron Lett. 1996, 37, 3501.
4. For other synthetic approaches to macrolactin A and related derivatives, see: (a) Rychnovsky, S. D.; Pickering, D. A. Abstracts of Papers, 207th National Meeting of the American Chemical Society, San Diego, CA; American Chemical Society: Washington, DC, 1994; ORGN 209 (b) Benvegnu, T.; Schio, L.; Le Floc'h, Y.; Grée, R. Synlett 1994, 505. (c) Benvegnu, T. J.; Toupet, L. J.; Grée, R. L. Tetrahedron 1996, 52, 11811. (d) Benvegnu, T. J.; Grée, R. L. Ibid. 1996, 52, 11821. (e) Donaldson, W. A.; Bell, P. T.; Wang, Z.; Bennett, D. W. Tetrahedron Lett. 1994, 35, 5829. (f) Prahlad, V.; Donaldson, W. A. Tetrahedron Lett. 1996, 37, 9169. (g) Tanimori, S.; Morita, Y.; Tsubota, M.; Nakayama, M. Synth. Commun. 1996, 26, 559. (h) González, Á.; Aiguadé, J.; Urpí, F.; Vilarrasa, J. Tetrahedron Lett. 1996, 37, 8949.
5. For other synthetic approaches to macrolactin A and related derivatives, see: (a) Rychnovsky, S. D.; Pickering, D. A. Abstracts of Papers, 207th National Meeting of the American Chemical Society, San Diego, CA; American Chemical Society: Washington, DC, 1994; ORGN 209 (b) Benvegnu, T.; Schio, L.; Le Floc'h, Y.; Grée, R. Synlett 1994, 505. (c) Benvegnu, T. J.; Toupet, L. J.; Grée, R. L. Tetrahedron 1996, 52, 11811. (d) Benvegnu, T. J.; Grée, R. L. Ibid. 1996, 52, 11821. (e) Donaldson, W. A.; Bell, P. T.; Wang, Z.; Bennett, D. W. Tetrahedron Lett. 1994, 35, 5829. (f) Prahlad, V.; Donaldson, W. A. Tetrahedron Lett. 1996, 37, 9169. (g) Tanimori, S.; Morita, Y.; Tsubota, M.; Nakayama, M. Synth. Commun. 1996, 26, 559. (h) González, Á.; Aiguadé, J.; Urpí, F.; Vilarrasa, J. Tetrahedron Lett. 1996, 37, 8949.
6. For other synthetic approaches to macrolactin A and related derivatives, see: (a) Rychnovsky, S. D.; Pickering, D. A. Abstracts of Papers, 207th National Meeting of the American Chemical Society, San Diego, CA; American Chemical Society: Washington, DC, 1994; ORGN 209 (b) Benvegnu, T.; Schio, L.; Le Floc'h, Y.; Grée, R. Synlett 1994, 505. (c) Benvegnu, T. J.; Toupet, L. J.; Grée, R. L. Tetrahedron 1996, 52, 11811. (d) Benvegnu, T. J.; Grée, R. L. Ibid. 1996, 52, 11821. (e) Donaldson, W. A.; Bell, P. T.; Wang, Z.; Bennett, D. W. Tetrahedron Lett. 1994, 35, 5829. (f) Prahlad, V.; Donaldson, W. A. Tetrahedron Lett. 1996, 37, 9169. (g) Tanimori, S.; Morita, Y.; Tsubota, M.; Nakayama, M. Synth. Commun. 1996, 26, 559. (h) González, Á.; Aiguadé, J.; Urpí, F.; Vilarrasa, J. Tetrahedron Lett. 1996, 37, 8949.
7. For other synthetic approaches to macrolactin A and related derivatives, see: (a) Rychnovsky, S. D.; Pickering, D. A. Abstracts of Papers, 207th National Meeting of the American Chemical Society, San Diego, CA; American Chemical Society: Washington, DC, 1994; ORGN 209 (b) Benvegnu, T.; Schio, L.; Le Floc'h, Y.; Grée, R. Synlett 1994, 505. (c) Benvegnu, T. J.; Toupet, L. J.; Grée, R. L. Tetrahedron 1996, 52, 11811. (d) Benvegnu, T. J.; Grée, R. L. Ibid. 1996, 52, 11821. (e) Donaldson, W. A.; Bell, P. T.; Wang, Z.; Bennett, D. W. Tetrahedron Lett. 1994, 35, 5829. (f) Prahlad, V.; Donaldson, W. A. Tetrahedron Lett. 1996, 37, 9169. (g) Tanimori, S.; Morita, Y.; Tsubota, M.; Nakayama, M. Synth. Commun. 1996, 26, 559. (h) González, Á.; Aiguadé, J.; Urpí, F.; Vilarrasa, J. Tetrahedron Lett. 1996, 37, 8949.
8. For other synthetic approaches to macrolactin A and related derivatives, see: (a) Rychnovsky, S. D.; Pickering, D. A. Abstracts of Papers, 207th National Meeting of the American Chemical Society, San Diego, CA; American Chemical Society: Washington, DC, 1994; ORGN 209 (b) Benvegnu, T.; Schio, L.; Le Floc'h, Y.; Grée, R. Synlett 1994, 505. (c) Benvegnu, T. J.; Toupet, L. J.; Grée, R. L. Tetrahedron 1996, 52, 11811. (d) Benvegnu, T. J.; Grée, R. L. Ibid. 1996, 52, 11821. (e) Donaldson, W. A.; Bell, P. T.; Wang, Z.; Bennett, D. W. Tetrahedron Lett. 1994, 35, 5829. (f) Prahlad, V.; Donaldson, W. A. Tetrahedron Lett. 1996, 37, 9169. (g) Tanimori, S.; Morita, Y.; Tsubota, M.; Nakayama, M. Synth. Commun. 1996, 26, 559. (h) González, Á.; Aiguadé, J.; Urpí, F.; Vilarrasa, J. Tetrahedron Lett. 1996, 37, 8949.
9. For other synthetic approaches to macrolactin A and related derivatives, see: (a) Rychnovsky, S. D.; Pickering, D. A. Abstracts of Papers, 207th National Meeting of the American Chemical Society, San Diego, CA; American Chemical Society: Washington, DC, 1994; ORGN 209 (b) Benvegnu, T.; Schio, L.; Le Floc'h, Y.; Grée, R. Synlett 1994, 505. (c) Benvegnu, T. J.; Toupet, L. J.; Grée, R. L. Tetrahedron 1996, 52, 11811. (d) Benvegnu, T. J.; Grée, R. L. Ibid. 1996, 52, 11821. (e) Donaldson, W. A.; Bell, P. T.; Wang, Z.; Bennett, D. W. Tetrahedron Lett. 1994, 35, 5829. (f) Prahlad, V.; Donaldson, W. A. Tetrahedron Lett. 1996, 37, 9169. (g) Tanimori, S.; Morita, Y.; Tsubota, M.; Nakayama, M. Synth. Commun. 1996, 26, 559. (h) González, Á.; Aiguadé, J.; Urpí, F.; Vilarrasa, J. Tetrahedron Lett. 1996, 37, 8949.
10. For other synthetic approaches to macrolactin A and related derivatives, see: (a) Rychnovsky, S. D.; Pickering, D. A. Abstracts of Papers, 207th National Meeting of the American Chemical Society, San Diego, CA; American Chemical Society: Washington, DC, 1994; ORGN 209 (b) Benvegnu, T.; Schio, L.; Le Floc'h, Y.; Grée, R. Synlett 1994, 505. (c) Benvegnu, T. J.; Toupet, L. J.; Grée, R. L. Tetrahedron 1996, 52, 11811. (d) Benvegnu, T. J.; Grée, R. L. Ibid. 1996, 52, 11821. (e) Donaldson, W. A.; Bell, P. T.; Wang, Z.; Bennett, D. W. Tetrahedron Lett. 1994, 35, 5829. (f) Prahlad, V.; Donaldson, W. A. Tetrahedron Lett. 1996, 37, 9169. (g) Tanimori, S.; Morita, Y.; Tsubota, M.; Nakayama, M. Synth. Commun. 1996, 26, 559. (h) González, Á.; Aiguadé, J.; Urpí, F.; Vilarrasa, J. Tetrahedron Lett. 1996, 37, 8949.
11. For other synthetic approaches to macrolactin A and related derivatives, see: (a) Rychnovsky, S. D.; Pickering, D. A. Abstracts of Papers, 207th National Meeting of the American Chemical Society, San Diego, CA; American Chemical Society: Washington, DC, 1994; ORGN 209 (b) Benvegnu, T.; Schio, L.; Le Floc'h, Y.; Grée, R. Synlett 1994, 505. (c) Benvegnu, T. J.; Toupet, L. J.; Grée, R. L. Tetrahedron 1996, 52, 11811. (d) Benvegnu, T. J.; Grée, R. L. Ibid. 1996, 52, 11821. (e) Donaldson, W. A.; Bell, P. T.; Wang, Z.; Bennett, D. W. Tetrahedron Lett. 1994, 35, 5829. (f) Prahlad, V.; Donaldson, W. A. Tetrahedron Lett. 1996, 37, 9169. (g) Tanimori, S.; Morita, Y.; Tsubota, M.; Nakayama, M. Synth. Commun. 1996, 26, 559. (h) González, Á.; Aiguadé, J.; Urpí, F.; Vilarrasa, J. Tetrahedron Lett. 1996, 37, 8949.
12. Preliminary communication: Smith, A. B., III; Ott, G. R. J. Am. Chem. Soc. 1996, 118, 13095.
13. A general theme of recent synthetic ventures of this laboratory exploits σ-bond constructions; for an overview see: Smith A. B., III; Condon S. M.; McCauley, J. A. Submitted for publication in Acc. Chem. Res.
14. (a) Stille, J. K. Angew. Chem., Int. Ed. Eng. 1986, 25, 508.
15. For a comprehensive review see: (b) Farina, V.; Krishnamurthy, V.; Scott, W. J. In Organic Reactions; Paquette, L. A., Ed.; John Wiley and Sons: New York, 1997; Vol. 50, pp 1-652.
16. See also: (c) Mitchell, T. N. Synthesis 1992, 803.
17. 13 see: (e) Paterson, I.; Man, J. Tetrahedron Lett. 1997, 38, 695.
18. 13 see: (e) Paterson, I.; Man, J. Tetrahedron Lett. 1997, 38, 695.
19. 13 see: (e) Paterson, I.; Man, J. Tetrahedron Lett. 1997, 38, 695.
20. 13 see: (e) Paterson, I.; Man, J. Tetrahedron Lett. 1997, 38, 695.
21. 13 see: (e) Paterson, I.; Man, J. Tetrahedron Lett. 1997, 38, 695.
22. (a) Barrett, A. G. M.; Boys, M. L.; Boehm, T. L. J. Org. Chem. 1996, 61, 685.
23. (b) McDermott, T. S.; Mortlock, A. A.; Heathcock, C. H. J. Org. Chem., 1996, 61, 700.
24. (c) Pattenden, G.; Thom, S. M. Synlett. 1993, 215.
25. (d) Boden, C.; Pattenden, G. Synlett 1994, 181.
26. (e) Kende, A. S.; Liu, K.; Kaldor, I.; Dorey, G.; Koch, K. J. Am. Chem. Soc. 1995, 117, 8258.
27. (f) Kende, A. S.; Koch, K.; Dorey, G.; Kaldor, I.; Liu, K. J. Am. Chem. Soc. 1993, 115, 9842
28. (g) Evans, D. A.; Black, W. C.; J. Am. Chem. Soc. 1992, 114, 2260.
29. (h) Smith, A. B., III; Condon, S. M.; McCauley, J. A.; Leazer, J. L., Jr.; Leahy, J. W.; Maleczka, R. E., Jr. J. Am. Chem. Soc. 1995, 117, 5407.
30. (i) Smith, A. B., III.; Condon, S. M.; McCauley, J. A.; Leazer, J. L., Jr.; Leahy, J. W.; Maleczka, R. E., Jr. Ibid. 1997, 119, 947.
31. (j) Smith, A. B., III; Condon, S. M.; McCauley, J. A.; Leazer, J. L., Jr.; Leahy, J. W.; Maleczka, R. E., Jr. Ibid. 1997, 119, 962.
32. Farina, V.; Krishnan, B.; J. Am. Chem. Soc. 1991, 113, 9585.
33. Srogl, J.; Allred, G. D.; Liebeskind, L. S. J. Am. Chem. Soc. 1997, 119, 12376.
34. Liebeskind, L. S.; Fengl, R. W. J. Org. Chem. 1990, 55, 5359. See also: Farina, V.; Kapadia, S.; Krishnan, B.; Wang, C. Liebeskind, L. S. J. Org. Chem. 1994, 59, 5905.
35. Liebeskind, L. S.; Fengl, R. W. J. Org. Chem. 1990, 55, 5359. See also: Farina, V.; Kapadia, S.; Krishnan, B.; Wang, C. Liebeskind, L. S. J. Org. Chem. 1994, 59, 5905.
36. For the use of stoichiometric copper(I) thiophene-2-carboxylate (CuTC) to effect Stille-type couplings see: Allred, G. D.; Liebeskind, L. S. J. Am. Chem. Soc. 1996, 118, 2748.
37. Mitsunobu, O. Synthesis 1981, 1.
38. (a) Zibuck, R.; Liverton, N. J.; Smith, A. B., III. J. Am. Chem. Soc. 1986, 108, 2451.
39. (b) Smith, A. B., III; Leahy, J. W.; Noda, I.; Remiszewski, S. W.; Liverton, N. J.; Zibuck, R. J. Am. Chem. Soc. 1992, 114, 2995.
40. Sauer, J. C. Organic Syntheses; Wiley: New York, 1963; Coll. Vol. IV, p 813.
41. (S)-5-Hexen-1-yn-3-ol has been resolved by lyophilized-yeast hydrolysis of the racemic acetate. Blänzer, B. I.; Faber, K.; Griengl, H. Tetrahedron 1987, 43, 5791.
42. Dale, J. A.; Mosher, H. S. J. Am. Chem. Soc. 1973, 95, 512.
43. Chen, S.-Y.; Joullié, M. M. Synth. Commun. 1984, 14, 591.
44. Takai, K.; Nitta, K.; Utimoto, K. J. Am. Chem. Soc. 1986, 108, 7408.
45. Barrett, A. G. M.; Pilipauskas, D. J. Org. Chem. 1990, 55, 5194.
46. Nuss, J. M.; Levine, B. H.; Rennels, R. A.; Heravi, M. M. Tetrahedron Lett. 1991, 32, 5243.
47. Zhang, Y.; Negishi, E. J. Am. Chem. Soc. 1989, 111, 3454.
48. (a) Hodgson, D. M. Tetrahedron Lett. 1992, 33, 5603.
49. (b) Hodgson, D. M.; Boulton, L. T.; Maw, G. N. Ibid. 1994, 35, 2231.
50. See also: (c) Cliff, M. D.; Pyne, S. G. Ibid. 1995, 36, 763.
51. Ma, S.; Lu, X.; Li, Z. J. Org. Chem. 1992, 57, 709.
52. Stille, J. K.; Groh, B. L. J. Am. Chem. Soc. 1987, 109, 813.
53. Zhang, H. X.; Guibé, F.; Balavoine, G. J. Org. Chem. 1990, 55, 1857.
54. (+)-16 was prepared in an analogous fashion as (-)-16 except that the opposite enantiomer (+)-B-methoxydiisopinocampheylborane was employed.
55. Pétrier, C.; Luche, J.-L. J. Org. Chem. 1985, 50, 910.
56. (a) Dess, D. B.; Martin, J. C. J. Org. Chem. 1983, 48, 4155.
57. (b) Reagent preparation: Ireland, R. E.; Liu, L. Ibid 1993, 58, 2899.
58. (a) Evans, D. A.; Chapman, K. T.; Carreira, E. M. J. Am. Chem. Soc. 1988, 110, 3560.
59. (b) Nutaitis, C. F.; Gribble, G. W. Tetrahedron Lett. 1983, 24, 4287.
60. 4 reductions in carboxylic acid media see (c) Gribble, G. W.; Nutaitis, C. F. Org. Proc. Prepr. Int. 1985, 17, 317.
61. 13C NMR analysis for assignment of 1,3-diol relative stereochemistry see: (a) Rychnovsky, S. D.; Skalitzky, D. J. Tetrahedron Lett. 1990, 31, 945. (b) Evans, D. A.; Rieger, D. L.; Gage, J. R. Ibid. 1990, 31, 7099. (c) Rychnovsky, S. D.; Rogers, B.; Yang, G. J. Org. Chem. 1993, 58, 3511. (d) Rychnovsky, S. D.; Yang, G.; Powers, J. P. Ibid. 1993, 58, 5251.
62. 13C NMR analysis for assignment of 1,3-diol relative stereochemistry see: (a) Rychnovsky, S. D.; Skalitzky, D. J. Tetrahedron Lett. 1990, 31, 945. (b) Evans, D. A.; Rieger, D. L.; Gage, J. R. Ibid. 1990, 31, 7099. (c) Rychnovsky, S. D.; Rogers, B.; Yang, G. J. Org. Chem. 1993, 58, 3511. (d) Rychnovsky, S. D.; Yang, G.; Powers, J. P. Ibid. 1993, 58, 5251.
63. 13C NMR analysis for assignment of 1,3-diol relative stereochemistry see: (a) Rychnovsky, S. D.; Skalitzky, D. J. Tetrahedron Lett. 1990, 31, 945. (b) Evans, D. A.; Rieger, D. L.; Gage, J. R. Ibid. 1990, 31, 7099. (c) Rychnovsky, S. D.; Rogers, B.; Yang, G. J. Org. Chem. 1993, 58, 3511. (d) Rychnovsky, S. D.; Yang, G.; Powers, J. P. Ibid. 1993, 58, 5251.
64. 13C NMR analysis for assignment of 1,3-diol relative stereochemistry see: (a) Rychnovsky, S. D.; Skalitzky, D. J. Tetrahedron Lett. 1990, 31, 945. (b) Evans, D. A.; Rieger, D. L.; Gage, J. R. Ibid. 1990, 31, 7099. (c) Rychnovsky, S. D.; Rogers, B.; Yang, G. J. Org. Chem. 1993, 58, 3511. (d) Rychnovsky, S. D.; Yang, G.; Powers, J. P. Ibid. 1993, 58, 5251.
65. Stork, G.; Zhao, K. Tetrahedron Lett. 1989, 30, 2173.
66. Millar, J. G.; Oehlschlager, A. C. J. Org. Chem. 1984, 49, 2332.
67. Catalyst prepared according to: Heck, R. F. Palladium Reagents in Organic Synthesis; Academic: New York, 1985; p 18.
68. Evans, D. A.; Gage, J. R.; Leighton, J. L. J. Am. Chem. Soc. 1992, 114, 9434.
69. Complete omission of ligands for Stille cross-couplings has been noted previously see: Beletskaya, I. P. J. Organomet. Chem. 1983, 250, 551.
70. Nicolaou, K. C.; Webber, S. E. Synthesis 1986, 453.
71. Corey, E. J.; Ponder, J. W.; Ulrich, P. Tetrahedron Lett. 1980, 21, 137.
72. (a) Pilcher, A. S.; Hill, D. K.; Shimshock, S. J.; Waltermire, R. E.; DeShong, P. J. Org. Chem. 1992, 57, 2492.
73. (b) Pilcher, A. S.; DeShong, P. Ibid. 1993, 58, 5130.
74. Macrolactin A was converted to macrolactinic acid using KOH/ MeOH. See reference 1.
75. (a) Greene, T. W.; Wutz, P. G. M. Protective Groups in Organic Synthesis; John Wiley and Sons: New York, 1991; p 73.
76. (b) Kocienski, P. J. Protecting Groups; George Thieme Verlag: New York, 1994; p 31.
77. (c) Nelson, T. D.; Crouch, R. D. Synthesis 1996, 1031.
78. To the best of our knowledge Otera and co-workers were the first to employ TBAF buffered with acetic acid to mitigate the basicity of fluoride to suppress β-elimination of a TBS ether, (a) Otera, J.; Niibo, Y.; Nozaki, H. Tetrahedron Lett. 1992, 33, 3655.
79. Smith, A. B., III.; Chen, S. S.-Y.; Nelson, F. C.; Reichert, J. M.; Salvatore, B. A. J. Am. Chem. Soc. 1995, 117, 12013. Danishefsky also exploited TBAF/HOAc in the synthesis of rapamycin; Hayward, C. M.; Yohannes, D.; Danishefsky, S. J. J. Am. Chem. Soc. 1993, 115, 9345.
80. Smith, A. B., III.; Chen, S. S.-Y.; Nelson, F. C.; Reichert, J. M.; Salvatore, B. A. J. Am. Chem. Soc. 1995, 117, 12013. Danishefsky also exploited TBAF/HOAc in the synthesis of rapamycin; Hayward, C. M.; Yohannes, D.; Danishefsky, S. J. J. Am. Chem. Soc. 1993, 115, 9345.
81. Fenical and co-workers prepared the triacetate derivative while performing the structure elucidation see ref 1.
82. 13C spectra.
83. Farina, V.; Hauck, S. I. J. Org. Chem. 1991, 56, 4317.
84. Corey, E. J.; Gilman, N. W.; Ganem, B. E. J. Am. Chem. Soc. 1968, 90, 5616.
85. Materials and Methods. All reactions were carried out in ovendried or flame-dried glassware under an argon atmosphere, unless otherwise noted. All solvents were reagent grade. Diethyl ether and tetrahydrofuran (THF) were freshly distilled from sodium/benzophenone under argon before use. Dichloromethane, benzene, hexamethylphosphoramide (HMPA), and trimethylsilyl chloride (TMSCl) were freshly distilled from calcium hydride before use. Triethylamine, pyridine, and diisopropylethylamine were distilled from calcium hydride and stored over potassium hydroxide. N,N-Dimethylformamide (DMF), N-methylpyrrollidinone (NMP), and 2,6-lutidine were freshly distilled and stored over 4 Å sieves. n-Butyllithium (n-BuLi) was purchased from Aldrich and standardized by titration with diphenylacetic acid. Deoxygenation was effected by bubbling argon through the reaction mixture for 15 min; the argon was deoxygenated by passing it through an "OXICLEAR" tube manufactured by Labclear, Oakland, CA. Unless stated otherwise, all reactions were magnetically stirred and monitored by thinlayer chromatography using 0.25 mm Whatman precoated silica gel plates. Flash column chromatography was performed with the indicated solvents using silica gel-60 (particle size 0.023-0.040 mm) supplied by E. Merck.