Applications of Zr-catalyzed carbomagnesation and Mo-catalyzed macrocyclic ring closing metathesis in asymmetric synthesis, enantioselective total synthesis of Sch 38516 (fluvirucin B 1)

Journal of the American Chemical Society

Volumn 119, Issue 43, 1997, Pages 10302-10316

  Xu, Zhongmin ^a   Johannes, Charles W ^a   Houri, Ahmad F ^a   La, Daniel S ^a   Cogan, Derek A ^a   Hofilena, Gloria E ^a   Hoveyda, Amir H ^a  

^a BOSTON COLLEGE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIFUNGAL AGENT; FLUVIRUCIN B1; SCH 38516; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; DRUG PURIFICATION; DRUG SYNTHESIS; IN VITRO STUDY; INFRARED SPECTROPHOTOMETRY; MASS SPECTROMETRY; METHODOLOGY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; STEREOCHEMISTRY; THIN LAYER CHROMATOGRAPHY;

EID: 0030700685     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja972191k     Document Type: Article

References (106)

1. Marston, W. The New York Times Magazine 1996, 11, 43-45.
2. (a) Hegde, V. R.; Patel, M. G.; Gullo, V. P.; Ganguly, A. K.; Sarre, O.; Puar, M. S.; McPhail, A. T. J. Am. Chem. Soc. 1990, 112, 6403-6405.
3. (b) Hegde, V. R.; Patel, M.; Horan, A.; Gullo, V.; Marquez, J.; Gunnarsson, I.; Gentile, F.; Loebenberg, D.; King, A. J. Antibiot. 1992, 45, 624-632.
4. (a) Naruse, N.; Tenmyo, O.; Kawano, K.; Tomita, K.; Ohgusa, N.; Miyaki, T.; Konishi, M.; Oki, T. J. Antibiot. 1991, 44, 733-740.
5. (b) Naruse, N.; Tsuno, T.; Sawada, Y.; Konishi, M.; Oki, T. J. Antibiot. 1991, 44, 741-755.
6. (c) Naruse, N.; Konishi, M.; Oki, T. J. Antibiot. 1991, 44, 756-761.
7. (d) Komita, K.; Oda, N.; Hoshino, Y.; Ohkusa, N.; Chikazawa, H. J. Antibiot. 1991, 44, 940-948.
8. (a) Hegde, V.; Patel, M. G.; Gullo, V. P.; Puar, M. S. J. Chem. Soc., Chem. Commun. 1991, 810-812.
9. (b) Hegde, V. R.; Patel, M. G.; Gullo, V. P.; Horan, A. C.; King, A. H.; Gentile, F.; Wagman, G. H.; Puar, M. S.; Loebenberg, D. J. Antibiot. 1993, 46, 1109-1115.
10. For preliminary accounts of this research, see: (a) Houri, A. F.; Xu, Z.; Cogan, D. A.; Hoveyda, A. H. J. Am. Chem. Soc. 1995, 117, 2943-2944. (b) Xu, Z.; Johannes, C. W.; Salman, S. S.; Hoveyda, A. H. J. Am. Chem. Soc. 1996, 118, 10926-10927. For an alternative approach to the macrolactam segment, see: Trost, B. M.; Ceschi, M. A.; König, B. Angew. Chem., Int. Ed. Engl. 1997, 36, 1486-1489.
11. For preliminary accounts of this research, see: (a) Houri, A. F.; Xu, Z.; Cogan, D. A.; Hoveyda, A. H. J. Am. Chem. Soc. 1995, 117, 2943-2944. (b) Xu, Z.; Johannes, C. W.; Salman, S. S.; Hoveyda, A. H. J. Am. Chem. Soc. 1996, 118, 10926-10927. For an alternative approach to the macrolactam segment, see: Trost, B. M.; Ceschi, M. A.; König, B. Angew. Chem., Int. Ed. Engl. 1997, 36, 1486-1489.
12. For preliminary accounts of this research, see: (a) Houri, A. F.; Xu, Z.; Cogan, D. A.; Hoveyda, A. H. J. Am. Chem. Soc. 1995, 117, 2943-2944. (b) Xu, Z.; Johannes, C. W.; Salman, S. S.; Hoveyda, A. H. J. Am. Chem. Soc. 1996, 118, 10926-10927. For an alternative approach to the macrolactam segment, see: Trost, B. M.; Ceschi, M. A.; König, B. Angew. Chem., Int. Ed. Engl. 1997, 36, 1486-1489.
13. (a) Corey, E. J.; Hopkins, P. B.; Kim, S.; Yoo, S.-E.; Nambia, K. P.; Falck, J. R. J. Am. Chem. Soc. 1979, 101, 7131-7134.
14. (b) Still, W. C.; Galynker, I. Tetrahedron 1981, 37, 3981-3996.
15. (c) Still, W. C.; Novack, V. J. J. Am. Chem. Soc. 1984, 106, 1148-1149.
16. (d) Schreiber, S. L.; Santini, C. J. Am. Chem. Soc. 1984, 106, 4038-4039.
17. (e) Neeland, E. G.; Ounsworth, J. P.; Sims, R. J.; Weiler, L. J. Org. Chem. 1994, 58, 7383-7394.
18. (f) Evans, D. A.; Ratz, A. M.; Huff, B. E.; Sheppard, S. G. J. Am. Chem. Soc. 1995, 117, 3448-3467.
19. For example, see: (a) Corey, E. J.; Weigel, L. O.; Chamberlin, A. R.; Cho, H.; Hua, D. H. J. Am. Chem. Soc. 1980, 102, 6613-6615. (b) Meyers, A. I.; Reider, P. J.; Campbell, A. L. J. Am. Chem. Soc. 1980, 102, 6597-6598.
20. For example, see: (a) Corey, E. J.; Weigel, L. O.; Chamberlin, A. R.; Cho, H.; Hua, D. H. J. Am. Chem. Soc. 1980, 102, 6613-6615. (b) Meyers, A. I.; Reider, P. J.; Campbell, A. L. J. Am. Chem. Soc. 1980, 102, 6597-6598.
21. (a) Hoveyda, A. H.; Xu, Z. J. Am. Chem. Soc. 1991, 113, 5079-5080.
22. (b) Hoveyda, A. H.; Xu, Z.; Morken, J. P.; Houri, A. F. J. Am. Chem. Soc. 1991, 113, 8950-8952.
23. (c) Houri, A. F.; Didiuk, M. T.; Xu, Z.; Horan, N. R.; Hoveyda, A. H. J. Am. Chem. Soc. 1993, 115, 6614-6624.
24. (d) Morken, J. P.; Hoveyda, A. H. J. Org. Chem. 1993, 4237-4244.
25. (a) Baldwin, J. E.; Adington, R. M.; Neil, I. A.; Schofield, C.; Spivey, A. C.; Sweeney, J. B. J. Chem. Soc., Chem. Commun. 1989, 1852-1854.
26. (b) Church, N. J.; Young, D. W. Tetrahedron Lett. 1995, 36, 151-154.
27. Corey, E. J.; Schaaf, T. K.; Huber, W.; Koelliker, U.; Weinshenker, N. M. J. Am. Chem. Soc. 1970, 92, 397-380.
28. (a) Fu, G. C.; Grubbs, R. H. J. Am. Chem. Soc. 1992, 114, 7324-7325.
29. (b) Fu, G. C.; Grubbs, R. H. J. Am. Chem. Soc. 1993, 115, 3800-3801.
30. (c) Grubbs, R. H.; Miller, S. J.; Fu, G. C. Acc. Chem. Res. 1995, 28, 446-452 and references cited therein.
31. (d) Schmalz, H.-G. Angew. Chem., Int. Ed. Engl. 1995, 107, 1981-1984 and references cited therein.
32. (a) Schrock, R. R.; Murdzek, J. S.; Bazan, G. C.; Robbins, J.; DiMare, M.; O'Regan, M. J. Am. Chem. Soc. 1990, 112, 3875-3886.
33. (b) Bazan, G. C.; Schrock, R. R.; Cho, H.-N.; Gibson, V. C. Macromolecules 1991, 24, 4495-4502.
34. Martin, S. F.; Liao, Y.; Wong, Y.; Rein, T. Tetrahedron Lett. 1994, 35, 691-694.
35. (c) Martin, S. F.; Liao, Y.; Chen, H.-J.; Patzel, M.; Ramser, M. N. Tetrahedron Lett. 1994, 35, 6005-6008.
36. Borer, B. C.; Deerenberg, S.; Bieraugel, H.; Pandit, U. K. Tetrahedron Lett. 1994, 35, 3191-3194.
37. Martin, S. F.; Liao, Y.; Chen, H.-J.; Patzel, M.; Ramser, M. N. Tetrahedron Lett. 1994, 35, 6005-6008.
38. Miller, S. J.; Kim, S.-H.; Chen, Z.-R.; Grubbs, R. H. J. Am. Chem. Soc. 1995, 117, 2108-2109.
39. For a classic example, see: Woodward, R. B. et al. J. Am. Chem. Soc. 1981, 3213-3215.
40. Recent elegant studies by Grubbs on the effect of stereochemistry on the synthesis of macrocyclic peptides (disubstituted alkenes) by ring closing metathesis were not disclosed at the time of our planning. See: (a) Miller, S. J.; Gubbs, R. H. J. Am. Chem. Soc. 1995, 117, 5855-5856. (b) Miller, S. J.; Blackwell, H.; Grubbs, R. H. J. Am. Chem. Soc. 1996, 118, 9606-9614.
41. Recent elegant studies by Grubbs on the effect of stereochemistry on the synthesis of macrocyclic peptides (disubstituted alkenes) by ring closing metathesis were not disclosed at the time of our planning. See: (a) Miller, S. J.; Gubbs, R. H. J. Am. Chem. Soc. 1995, 117, 5855-5856. (b) Miller, S. J.; Blackwell, H.; Grubbs, R. H. J. Am. Chem. Soc. 1996, 118, 9606-9614.
42. (a) Gao, Y.; Hanson, R. M.; Klunder, J. M.; Ko, S. Y.; Masamune, H.; Sharpless, K. B. J. Am. Chem. Soc. 1987, 109, 5765-5780.
43. For a comprehensive review, see: (b) Johnson, R. A.; Sharpless, K. B. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: New York, 1993; pp 103-158.
44. For an unusually facile eight-membered ring synthesis through catalytic metathesis, see: (a) Visser, M. S.; Heron, N. M.; Didiuk, M. T.; Sagal, J. F.; Hoveyda, A. H. J. Am. Chem. Soc. 1996, 118, 4291-4298. For a more recent related study, see: (b) Linderman, R. J.; Siedlecki, J.; O'Neill, S. A.; Sun, H. J. Am. Chem. Soc. 1997, 119, 6919-6920.
45. For an unusually facile eight-membered ring synthesis through catalytic metathesis, see: (a) Visser, M. S.; Heron, N. M.; Didiuk, M. T.; Sagal, J. F.; Hoveyda, A. H. J. Am. Chem. Soc. 1996, 118, 4291-4298. For a more recent related study, see: (b) Linderman, R. J.; Siedlecki, J.; O'Neill, S. A.; Sun, H. J. Am. Chem. Soc. 1997, 119, 6919-6920.
46. (a) Morken, J. P.; Didiuk, M. T.; Hoveyda, A. H. J. Am. Chem. Soc. 1993, 115, 6697-6698.
47. (b) Reference 20. For a recent review, see: Hoveyda, A. H.; Morken, J. P. Angew. Chem., Int. Ed. Engl. 1996, 35, 1262-1284.
48. (a) Eisch, J. J.; Galle, J. E. J. Organomet. Chem. 1978, 160, C8-C12.
49. (b) Sato, F. J. Organomet. Chem. 1985, 185, 53-64.
50. Tamao, K.; Sumitani, K.; Kumada, M. J. Am. Chem. Soc. 1972, 94, 4374-4376.
51. Ley, S. V.; Norman, J.; Griffith, W. P.; Marsden, S. P. Synthesis 1994, 639-666 and references cited therein.
52. Li, W. R.; Ewing, W. R.; Harris, B. D.; Joullie, M. J. Am. Chem. Soc. 1990, 112, 7659-7672.
53. It is likely that, as recently demonstrated by Furstner, higher yields of the disubstituted olefin 35 may be obtained under strict high dilution conditions and with longer reaction times. Our experiments clearly illustrate that the synthesis of trisubstituted macrocyclic alkenes is significantly more demanding than that of their disubstituted analogues. See: Furstner, A.; Langemann, K. J. Org. Chem. 1996, 61, 3942-3943.
54. Marsella, M. J.; Maynard, H. D.; Grubbs, R. H. Angew. Chem., Int. Ed. Engl. 1997, 36, 1101-1103 and references cited therein.
55. A synthesis of the carbohydrate, 3-amino-3,6-deoxy-D-talopyranose, was disclosed by Stanek and Jary in 1974. Their reported procedure affords the amino sugar only as a byproduct, formed en route to a mixture of various 3-amino-3,6-pyranoses (2.4% of total mixture). See: Capek, K; Stanek, J.; Jary, J. Coll. Czech. Chem. Commun. 1974, 39, 1462-1478.
56. DeShong, P.; Dicken, C. M.; Leginus, J. M.; Whittle, R. R. J. Am. Chem. Soc. 1984, 106, 5598-5602 and references cited therein.
57. (a) Pedersen, S. F.; Konradi, A. W. J. Org. Chem. 1990, 55, 4506-4508.
58. (b) Hauser, F.; Ellenberger, S. R. J. Org. Chem. 1986, 51, 50-57.
59. (c) Fuganti, C.; Grasselli, P.; Pedrocchi-Fantoni, G. J. Org. Chem. 1983, 48, 909-910.
60. (a) Mukaiyama, T.; Goto, Y.; Shoda, S. Chem. Lett. 1983, 671-674.
61. (b) Fuganti, C.; Grasselli, P.; Pedrocchi-Fantoni, G. J. Org. Chem. 1983, 48, 910-912.
62. Binder, W. H.; Prenner, R. H.; Schmid, W. Monat. Chem. 1994, 125, 763-771.
63. (a) Xu, D.; Crispino, G.; Sharpless, K. B. J. Am. Chem. Soc. 1992, 114, 7570-7571.
64. (b) Kolb, H. C.; VanNiemvehze, M. S.; Sharpless, K. B. Chem. Rev. 1994, 94, 2483-2547.
65. Direct ozonolytic cleavage of protected 43 affords 45 in 40% isolated yield (versus 64% for the two-step sequence shown in Scheme 10).
66. Conditions originally reported by DeShong are 30 equiv of vinylene carbonate, 95°C, 72 h (cf. ref 29).
67. (a) Wovkulich, P. M.; Uskokovic, M. R. J. Am. Chem. Soc. 1989, 111, 3956-3957 and references cited therein.
68. For other related examples, see: (b) Belzecki, C.; Panfil, C. J. Org. Chem. 1979, 44, 1212-1216. (c) Vasella, A.; Voeffray, R. Helv. Chim. Acta. 1982, 65, 1134-1137 and references cited therein, (d) Kita, Y.; Itoh, F.; Tamura, O.; Ke, Y. Y. Tetrahedron Lett. 1987, 28, 1431-1434.
69. For other related examples, see: (b) Belzecki, C.; Panfil, C. J. Org. Chem. 1979, 44, 1212-1216. (c) Vasella, A.; Voeffray, R. Helv. Chim. Acta. 1982, 65, 1134-1137 and references cited therein, (d) Kita, Y.; Itoh, F.; Tamura, O.; Ke, Y. Y. Tetrahedron Lett. 1987, 28, 1431-1434.
70. For other related examples, see: (b) Belzecki, C.; Panfil, C. J. Org. Chem. 1979, 44, 1212-1216. (c) Vasella, A.; Voeffray, R. Helv. Chim. Acta. 1982, 65, 1134-1137 and references cited therein, (d) Kita, Y.; Itoh, F.; Tamura, O.; Ke, Y. Y. Tetrahedron Lett. 1987, 28, 1431-1434.
71. For synthesis of the chiral hydroxylamine, see: Polonski, T.; Chimiak, A. Tetrahedron Lett. 1974, 2453-2456.
72. For the use of this chiral auxiliary in stereoselective reactions with O-silylketene acetals, see ref 36d.
73. (a) Bjorgo, J.; Boyd, D. R.; Neill, D. C. J. Chem. Soc, Chem. Commun. 1974, 478-479.
74. Energy differences between E and Z nitrones have been measured: (b) Breuer, E.; Aurich, H.; Nielsen, A. In Nitrones, Nitronates and Nitroxides; John Wiley & Sons: New York, 1989; p 151.
75. Firestone, R. A. J. Org. Chem. 1968, 33, 2285-2290 and references cited therein.
76. (a) Huisgen, R. Angew. Chem., Int. Ed. Engl. 1963, 2, 633-645.
77. (b) Professor K. N. Houk, personal communication.
78. Houk, K. N. Acc. Chem. Res. 1975, 8, 361-369.
79. (a) Anh, N. T.; Eisenstein, O. Nouv. J. Chim. 1977, 1, 61-70.
80. (b) Houk, K. N.; Paddon-Row, M. N.; Rondan, N. G.; Wu, Y.-D.; Brown, F. K.; Spellmeyer, D. C.; Metz, J. T.; Li, Y.; Loncharich, R. J. Science 1986, 231, 1108-1117 and references cited therein.
81. 2, Raney Ni, MeOH (14 h) afforded a complex mixture of unidentifiable products.
82. Pearlman, M. W. Tetrahedron Lett. 1967, 17, 1663-1664.
83. Several additional issues in connection to the transformation depicted in Scheme 16 merit comment: (1) In the formation of the intermediate methoxyacetal, the initial product consists of a 3:1 mixture of α:β isomers (after 8 h); however, after prolonged reaction times (70 h), the a anomer becomes the sole product. (2) Whereas formation of the above mentioned α-methylacetal requires 70 h, that of daunosamine (lacking the C2 axial OH) is complete within 30 min. This rate difference may be due to destabilization of the intermediate oxonium ion by the axially disposed hydroxide.
84. (a) Dahmen, J.; Frejd, T.; Mangusson, G.; Noori, G. Carbohydr. Res. 1983, 114, 328-330.
85. (b) Gurjar, M. K.; Viswanadham, G. Tetrahedron Lett. 1991, 32, 6191-6194.
86. Pozsgay, V. J. Chem. Soc. 1995, 117, 6673-6681.
87. 2O used was freshly distilled, it is tenable that HF contamination gives rise to the observed intramolecular etherification.
88. Mukaiyama, T.; Katsurada, M.; Takashima, T. Chem. Lett. 1991, 985-988.
89. (a) Mukaiyama, T.; Murai, Y.; Shoda, S. Chem. Lett. 1981, 431-432.
90. (b) Mukaiyama, T.; Hashimoto, Y.; Shoda, S. Chem. Lett. 1983, 935-938.
91. (a) Nicolaou, K. C.; Dolle, R. E.; Papahatjis, D. P.; Randall, J. L.; J. Am. Chem. Soc. 1984, 106, 4189-4192.
92. (b) Nicolaou, K. C.; Randall, J. L.; Furst, G. T. J. Am. Chem. Soc. 1985, 107, 5556-5558.
93. Diene carbinol 62 may also be prepared by direct coupling of the amine derived from 22 (cf. Scheme 4) with carboxylic acid 18 (cf. Scheme 6). However, this procedure is significantly lower yielding than reaction with silylated derivative 17 (85% vs 55-60%). The difference in efficiency likely arises from difficulties in the purification of 22 prior to the coupling procedure.
94. (a) Bertinato, P.; Sorensen, E. J.; Meng, D.; Danishefsky, S. J. J. Org. Chem. 1996, 61, 8000-8001.
95. (b) Meng, D.; Su, D.-S.; Balog, A.; Bertinato, P.; Sorensen, E. J.; Danishefsky, S. J.; Zheng, Y.-H.; Chou, T.-C.; He, L.; Horwitz, S. B. J. Am. Chem. Soc. 1997, 119, 2733-2734.
96. (a) Nicolaou, K. C.; He, Y.; Vourloumis, D.; Vallberg, H.; Yang, Z. Angew. Chem., Int. Ed. Engl. 1996, 35, 2399-2401.
97. (b) Yang, Z.; He, Y.; Vourloumis, D.; Vallberg, H.; Nicolaou, K. C. Angew. Chem., Int. Ed. Engl. 1997, 36, 166-168.
98. (c) Nicolaou, K. C.; Sarabia, F.; Ninkovic, S.; Yang, Z. Angew. Chem., Int. Ed. Engl. 1997, 36, 525-527.
99. (d) Nicolaou, K. C.; Winssinger, N.; Pastor, J.; Ninkovic, S.; Sarabia, F.; He, Y.; Vourloumis, D.; Yang, Z.; Li, T.; Giannakakou, P.; Hamel, E. Nature 1997, 387, 268-272.
100. Kim, S. H.; Figueroa, I.; Fuchs, P. L. Tetrahedron Lett. 1997, 38, 2601-2604.
101. Furstner, A.; Kindler, N. Tetrahedron Lett. 1996, 37, 7005-7008.
102. Schinzer, D.; Limberg, A.; Bauer, A.; Bohm, O. M.; Cordes, M. Angew. Chem., Int. Ed. Engl. 1997, 36, 523-524.
103. More recent accounts from the laboratories of Grubbs and Sauvage indicate that the metathesis technology may be readily applied to the synthesis of marcocyclic crown ethers and [2]catenanes. See: (a) Marsella, M. J.; Maynard, H. D.; Grubbs, R. H. Angew. Chem., Int. Ed. Engl. 1997, 36, 1101-1103.
104. (b) Mohr, B.; Weck, M.; Sauvage, J.-P.; Grubbs, R. H. Angew. Chem., Int. Ed. Engl. 1997, 36, 1308-1310.
105. General experimental information for select reagents and compounds not involved in the final synthesis route and copies of spectral data for all synthetic intermediates can be found in the Supporting Information section.
106. 3N.