Synthesis of a protected (±)-calicheamicinone derivative by sequential introduction of functionality into the bicyclo[7.3.1]enediyne core structure

Journal of the American Chemical Society

Volumn 119, Issue 29, 1997, Pages 6739-6748

  Magnus, Philip ^a   Miknis, Gregory F ^a   Press, Neil J ^a   Grandjean, Didier ^a   Taylor, G Mark ^a   Harling, John ^a  

^a UNIVERSITY OF TEXAS AT AUSTIN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC ANTIBIOTIC; BICYCLO COMPOUND; CALICHEAMICIN DERIVATIVE;

AMINATION; ARTICLE; DRUG SYNTHESIS; OXIDATION; X RAY CRYSTALLOGRAPHY;

EID: 0030748827     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja970743t     Document Type: Article

References (76)

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22. For a recent extensive review, see: Lhermitte, H.; Grierson, D. S. Contemporary Organic Synthesis 1996, 3, 41 and 1996, 3, 93. Kende, A. S.; Smith, C. A. Tetrahedron Lett. 1988, 29, 4217. Schreiber, S. L.; Kiessling, L. L. J. Am. Chem. Soc. 1988, 110, 631. Schreiber, S. L.; Kiessling, L. L. Tetrahedron Lett. 1989, 30, 433. Maier, M. E.; Brandstetter, T. Tetrahedron Lett. 1992, 33, 7511. Maier, M. E.; Brandstetter, T. Liebigs Ann. Chem. 1993, 1009. Tomioka, K.; Fujita, H.; Koga, K. Tetrahedron Lett. 1989, 30, 851.
23. For a recent extensive review, see: Lhermitte, H.; Grierson, D. S. Contemporary Organic Synthesis 1996, 3, 41 and 1996, 3, 93. Kende, A. S.; Smith, C. A. Tetrahedron Lett. 1988, 29, 4217. Schreiber, S. L.; Kiessling, L. L. J. Am. Chem. Soc. 1988, 110, 631. Schreiber, S. L.; Kiessling, L. L. Tetrahedron Lett. 1989, 30, 433. Maier, M. E.; Brandstetter, T. Tetrahedron Lett. 1992, 33, 7511. Maier, M. E.; Brandstetter, T. Liebigs Ann. Chem. 1993, 1009. Tomioka, K.; Fujita, H.; Koga, K. Tetrahedron Lett. 1989, 30, 851.
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25. 6-Acetylene Complexes for the Synthesis of Enediyne Antitumor Antibiotics. SmithKline Beecham Research Symposium, Organometallic Reagents in Organic Synthesis; Academic Press Ltd.: 1994; Chapter 1, p 1.
26. 6-Acetylene Complexes for the Synthesis of Enediyne Antitumor Antibiotics. SmithKline Beecham Research Symposium, Organometallic Reagents in Organic Synthesis; Academic Press Ltd.: 1994; Chapter 1, p 1.
27. Kadow, J. F.; Tun, M. M.; Vyas, D. M.; Wittman, M. D.; Doyle, T. W. Tetrahedron Lett. 1992, 33, 1423. Kadow, J. F.; Cook, D. J.; Doyle, T. W.; Langley, D. R.; Pham, K. M.; Vyas, D. M.; Wittman, M. D. Tetrahedron 1994, 50, 1519. Dr. John Kadow is thanked for exchanges of information concerning the conversion of 16 into 20.
28. Kadow, J. F.; Tun, M. M.; Vyas, D. M.; Wittman, M. D.; Doyle, T. W. Tetrahedron Lett. 1992, 33, 1423. Kadow, J. F.; Cook, D. J.; Doyle, T. W.; Langley, D. R.; Pham, K. M.; Vyas, D. M.; Wittman, M. D. Tetrahedron 1994, 50, 1519. Dr. John Kadow is thanked for exchanges of information concerning the conversion of 16 into 20.
29. Magnus, P.; Lewis, R. T.; Bennett, F. J. Chem. Soc., Chem. Commun. 1989, 916. Magnus, P.; Lewis, R.; Bennett, F. J. Am. Chem. Soc. 1992, 114, 2560.
30. Magnus, P.; Lewis, R. T.; Bennett, F. J. Chem. Soc., Chem. Commun. 1989, 916. Magnus, P.; Lewis, R.; Bennett, F. J. Am. Chem. Soc. 1992, 114, 2560.
31. Treatment of the diol 33 with thiolacetic acid under Mitsunobu conditions gave the cyclic ether 33a (70%). Using the modified reaction conditions reported by Danishefsky (ref 2) also gave 33a. Consequently, we were forced to proceed by the protection deprotection sequence depicted in Scheme 4, as were both Nicolaou and Clive (refs 3 and 4), but using different protecting groups. (Matrix Presented)
32. The efforts to introduce the C2-amino group into 7 has lead to a number of new reactions involving PhIO/trimethylsilyl azide chemistry and other electrophilic aminating species. Magnus, P.; Lacour, J.; Evans, P. A.; Roe, M. B.; Hulme, C. J. Am. Chem. Soc. 1996, 118, 3406. Magnus, P.; Lacour, J. J. Am. Chem. Soc. 1992, 114, 3993. Magnus, P.; Lacour, J.; Coldham, I.; Mugrage, B.; Bauta, W. B. Tetrahedron, 1995, 51, 11087. Magnus, P.; Barth, L. Tetrahedron 1995, 51, 11075. Magnus, P.; Lacour, J.; Weber, W. J. Am. Chem. Soc. 1993, 115, 9347. Magnus, P.; Hulme, C.; Weber. W. J. Am. Chem. Soc. 1994, 116, 4501.
33. The efforts to introduce the C2-amino group into 7 has lead to a number of new reactions involving PhIO/trimethylsilyl azide chemistry and other electrophilic aminating species. Magnus, P.; Lacour, J.; Evans, P. A.; Roe, M. B.; Hulme, C. J. Am. Chem. Soc. 1996, 118, 3406. Magnus, P.; Lacour, J. J. Am. Chem. Soc. 1992, 114, 3993. Magnus, P.; Lacour, J.; Coldham, I.; Mugrage, B.; Bauta, W. B. Tetrahedron, 1995, 51, 11087. Magnus, P.; Barth, L. Tetrahedron 1995, 51, 11075. Magnus, P.; Lacour, J.; Weber, W. J. Am. Chem. Soc. 1993, 115, 9347. Magnus, P.; Hulme, C.; Weber. W. J. Am. Chem. Soc. 1994, 116, 4501.
34. The efforts to introduce the C2-amino group into 7 has lead to a number of new reactions involving PhIO/trimethylsilyl azide chemistry and other electrophilic aminating species. Magnus, P.; Lacour, J.; Evans, P. A.; Roe, M. B.; Hulme, C. J. Am. Chem. Soc. 1996, 118, 3406. Magnus, P.; Lacour, J. J. Am. Chem. Soc. 1992, 114, 3993. Magnus, P.; Lacour, J.; Coldham, I.; Mugrage, B.; Bauta, W. B. Tetrahedron, 1995, 51, 11087. Magnus, P.; Barth, L. Tetrahedron 1995, 51, 11075. Magnus, P.; Lacour, J.; Weber, W. J. Am. Chem. Soc. 1993, 115, 9347. Magnus, P.; Hulme, C.; Weber. W. J. Am. Chem. Soc. 1994, 116, 4501.
35. The efforts to introduce the C2-amino group into 7 has lead to a number of new reactions involving PhIO/trimethylsilyl azide chemistry and other electrophilic aminating species. Magnus, P.; Lacour, J.; Evans, P. A.; Roe, M. B.; Hulme, C. J. Am. Chem. Soc. 1996, 118, 3406. Magnus, P.; Lacour, J. J. Am. Chem. Soc. 1992, 114, 3993. Magnus, P.; Lacour, J.; Coldham, I.; Mugrage, B.; Bauta, W. B. Tetrahedron, 1995, 51, 11087. Magnus, P.; Barth, L. Tetrahedron 1995, 51, 11075. Magnus, P.; Lacour, J.; Weber, W. J. Am. Chem. Soc. 1993, 115, 9347. Magnus, P.; Hulme, C.; Weber. W. J. Am. Chem. Soc. 1994, 116, 4501.
36. The efforts to introduce the C2-amino group into 7 has lead to a number of new reactions involving PhIO/trimethylsilyl azide chemistry and other electrophilic aminating species. Magnus, P.; Lacour, J.; Evans, P. A.; Roe, M. B.; Hulme, C. J. Am. Chem. Soc. 1996, 118, 3406. Magnus, P.; Lacour, J. J. Am. Chem. Soc. 1992, 114, 3993. Magnus, P.; Lacour, J.; Coldham, I.; Mugrage, B.; Bauta, W. B. Tetrahedron, 1995, 51, 11087. Magnus, P.; Barth, L. Tetrahedron 1995, 51, 11075. Magnus, P.; Lacour, J.; Weber, W. J. Am. Chem. Soc. 1993, 115, 9347. Magnus, P.; Hulme, C.; Weber. W. J. Am. Chem. Soc. 1994, 116, 4501.
37. The efforts to introduce the C2-amino group into 7 has lead to a number of new reactions involving PhIO/trimethylsilyl azide chemistry and other electrophilic aminating species. Magnus, P.; Lacour, J.; Evans, P. A.; Roe, M. B.; Hulme, C. J. Am. Chem. Soc. 1996, 118, 3406. Magnus, P.; Lacour, J. J. Am. Chem. Soc. 1992, 114, 3993. Magnus, P.; Lacour, J.; Coldham, I.; Mugrage, B.; Bauta, W. B. Tetrahedron, 1995, 51, 11087. Magnus, P.; Barth, L. Tetrahedron 1995, 51, 11075. Magnus, P.; Lacour, J.; Weber, W. J. Am. Chem. Soc. 1993, 115, 9347. Magnus, P.; Hulme, C.; Weber. W. J. Am. Chem. Soc. 1994, 116, 4501.
38. Magnus, P.; Eisenbeis, S. A.; Fairhurst, R. A.; Iliadis, T.; Magnus, N. A.; Parry, D. J. Am. Chem. Soc. 1997, 119, 5591-5605.
39. Stephens, R. D.; Castro, C. E. J. Org. Chem. 1963, 28, 3313. Ratovelomanana, V.; Linstrumelle, G. Tetrahedron Lett. 1984, 25, 6001. Guillerm, D.; Linstrumelle, G. Tetrahedron Lett. 1986, 27, 5857. Guillerm. D.; Linstumelle, G. Tetrahedron Lett. 1985, 26, 3811.
40. Stephens, R. D.; Castro, C. E. J. Org. Chem. 1963, 28, 3313. Ratovelomanana, V.; Linstrumelle, G. Tetrahedron Lett. 1984, 25, 6001. Guillerm, D.; Linstrumelle, G. Tetrahedron Lett. 1986, 27, 5857. Guillerm. D.; Linstumelle, G. Tetrahedron Lett. 1985, 26, 3811.
41. Stephens, R. D.; Castro, C. E. J. Org. Chem. 1963, 28, 3313. Ratovelomanana, V.; Linstrumelle, G. Tetrahedron Lett. 1984, 25, 6001. Guillerm, D.; Linstrumelle, G. Tetrahedron Lett. 1986, 27, 5857. Guillerm. D.; Linstumelle, G. Tetrahedron Lett. 1985, 26, 3811.
42. Stephens, R. D.; Castro, C. E. J. Org. Chem. 1963, 28, 3313. Ratovelomanana, V.; Linstrumelle, G. Tetrahedron Lett. 1984, 25, 6001. Guillerm, D.; Linstrumelle, G. Tetrahedron Lett. 1986, 27, 5857. Guillerm. D.; Linstumelle, G. Tetrahedron Lett. 1985, 26, 3811.
43. Tsuji, J.; Minami, I.; Shimizu, I.; Kataoka, H. Chem. Lett. 1984, 1133. Shimizu, I.; Tsuji, J. J. Am. Chem. Soc. 1982, 104, 5844.
44. Tsuji, J.; Minami, I.; Shimizu, I.; Kataoka, H. Chem. Lett. 1984, 1133. Shimizu, I.; Tsuji, J. J. Am. Chem. Soc. 1982, 104, 5844.
45. 6-proparglic alcohol see: Marshall, J. A.; Gung, W. Y. Tetrahedron Lett. 1989, 30, 309. Narasaka, K.; Morikawa, A.; Saigo, K.; Mukaiyama, T. Bull. Chem. Soc. Jpn. 1977, 50, 2773. Meyers, A. I.; Comins, D. L.; Roland, D. M.; Henning, R.; Shimizu, K. J. Am. Chem. Soc. 1978, 101, 7104.
46. 6-proparglic alcohol see: Marshall, J. A.; Gung, W. Y. Tetrahedron Lett. 1989, 30, 309. Narasaka, K.; Morikawa, A.; Saigo, K.; Mukaiyama, T. Bull. Chem. Soc. Jpn. 1977, 50, 2773. Meyers, A. I.; Comins, D. L.; Roland, D. M.; Henning, R.; Shimizu, K. J. Am. Chem. Soc. 1978, 101, 7104.
47. 6-proparglic alcohol see: Marshall, J. A.; Gung, W. Y. Tetrahedron Lett. 1989, 30, 309. Narasaka, K.; Morikawa, A.; Saigo, K.; Mukaiyama, T. Bull. Chem. Soc. Jpn. 1977, 50, 2773. Meyers, A. I.; Comins, D. L.; Roland, D. M.; Henning, R.; Shimizu, K. J. Am. Chem. Soc. 1978, 101, 7104.
48. Itoh, A.; Ozawa, S.; Oshima, K.; Nozaki, H. Bull. Chem. Soc. Jpn. 1981, 54, 274.
49. Nicolaou, K. C.; Claremon, D. A.; Barnette, W. E.; Seitz, S. P. J. Am. Chem. Soc. 1979, 101, 3704. Nicolaou, K. C.; Petasis, N. A.; Claremon, D. A. Tetrahedron 1985, 41, 4835.
50. Nicolaou, K. C.; Claremon, D. A.; Barnette, W. E.; Seitz, S. P. J. Am. Chem. Soc. 1979, 101, 3704. Nicolaou, K. C.; Petasis, N. A.; Claremon, D. A. Tetrahedron 1985, 41, 4835.
51. Our earlier work on the 12-desoxy series had shown that treatment of (i) with N-(phenylselenenyl)phthalimide/DBU gave the monoselenide (ii), which on oxidation provided access to the 3β-ol (iii). Magnus, P.; Lewis, R.; Bennett, F. J. Am. Chem. Soc. 1992, 114, 2560. (Matrix Presented)
52. The best results were obtained with W-(phenylselenenyl)phthalimide that was crystallized to constant melting point. While we could not detect impurities by TLC and NMR, the yields with unpurified reagent were <30%, and sometimes the substrate 21 was completely destroyed.
53. Magnus, P.; Barth, L. Tetrahedron 1995, 51, 11075. Patonay, T.; Hoffman, R. V. J. Org. Chem. 1995, 60, 2368. Effenberger, F.; Beisswenger, T.; Az, R. Chem. Ber. 1985, 118, 4869. Effenberger, F.; Beisswenger, T. Chem. Ber. 1984, 117, 1497. α-Azidoketones (iv) undergo elimination of nitrogen to give an imine (v), which usually tautomerizes to the enamine (vi). (Matrix Presented)
54. Magnus, P.; Barth, L. Tetrahedron 1995, 51, 11075. Patonay, T.; Hoffman, R. V. J. Org. Chem. 1995, 60, 2368. Effenberger, F.; Beisswenger, T.; Az, R. Chem. Ber. 1985, 118, 4869. Effenberger, F.; Beisswenger, T. Chem. Ber. 1984, 117, 1497. α-Azidoketones (iv) undergo elimination of nitrogen to give an imine (v), which usually tautomerizes to the enamine (vi). (Matrix Presented)
55. Magnus, P.; Barth, L. Tetrahedron 1995, 51, 11075. Patonay, T.; Hoffman, R. V. J. Org. Chem. 1995, 60, 2368. Effenberger, F.; Beisswenger, T.; Az, R. Chem. Ber. 1985, 118, 4869. Effenberger, F.; Beisswenger, T. Chem. Ber. 1984, 117, 1497. α-Azidoketones (iv) undergo elimination of nitrogen to give an imine (v), which usually tautomerizes to the enamine (vi). (Matrix Presented)
56. Magnus, P.; Barth, L. Tetrahedron 1995, 51, 11075. Patonay, T.; Hoffman, R. V. J. Org. Chem. 1995, 60, 2368. Effenberger, F.; Beisswenger, T.; Az, R. Chem. Ber. 1985, 118, 4869. Effenberger, F.; Beisswenger, T. Chem. Ber. 1984, 117, 1497. α-Azidoketones (iv) undergo elimination of nitrogen to give an imine (v), which usually tautomerizes to the enamine (vi). (Matrix Presented)
57. 3/MeOH a low yield of the triazole 23a resulted. (Matrix Presented)
58. Furukawa, N.; Yoshimura, T.; Ohtsu, M.; Akasaka, T.; Oae, S. Tetrahedron 1980, 36, 73. Yoshimura, T.; Omata, T.; Furukawa, N.; Oae, S. J. Org. Chem. 1976, 41, 1728.
59. Furukawa, N.; Yoshimura, T.; Ohtsu, M.; Akasaka, T.; Oae, S. Tetrahedron 1980, 36, 73. Yoshimura, T.; Omata, T.; Furukawa, N.; Oae, S. J. Org. Chem. 1976, 41, 1728.
60. 2S=NH reacts with similar enones to give an aziridine. Clark, D. A.; De Riccardis, F.; Nicolaou, K. C. Tetrahedron 1994, 50, 11391. Ulibarri, G.; Nadler, W.; Skrydstrup, T.; Audrain, H.; Chiaroni, A.; Riche, C.; Grierson, D. S. J. Org. Chem. 1995, 60, 2753.
61. 2S=NH reacts with similar enones to give an aziridine. Clark, D. A.; De Riccardis, F.; Nicolaou, K. C. Tetrahedron 1994, 50, 11391. Ulibarri, G.; Nadler, W.; Skrydstrup, T.; Audrain, H.; Chiaroni, A.; Riche, C.; Grierson, D. S. J. Org. Chem. 1995, 60, 2753.
62. Wadsworth, W. S.; Emmons, W. D. J. Am. Chem. Soc. 1961, 83, 1733.
63. Rathke, M. W.; Nowak, M. J. Org. Chem. 1985, 50, 2624.
64. 2S=NH under the conditions that worked well for the enedione 26. More vigorous reaction conditions gave extensive decomposition.
65. Letsinger, R. L.; Fontaine, J.; Mahadevan, V.; Schexnayder, D. A.; Leone, R. E. J. Org. Chem. 1964, 29, 2615.
66. Harpp, D. N. Studies in Organic Chemistry 28. Perspectives in The Organic Chemistry of Sulfur; Zwanenburg, B., Klunder, A. H., Eds.; Elsevier: Amsterdam, 1987. Harpp, D. N.; Steliou, K.; Chen, T. H. J. Am. Chem. Soc. 1978, 100, 1222. Harpp, D. N.; Ash, D. K. Int. J. Sulfur. Chem. A 1971, 1, 211. Harpp, D. N.; Ash, D. K. Int. J. Sulfur. Chem. A 1971, 1, 57.
67. Harpp, D. N. Studies in Organic Chemistry 28. Perspectives in The Organic Chemistry of Sulfur; Zwanenburg, B., Klunder, A. H., Eds.; Elsevier: Amsterdam, 1987. Harpp, D. N.; Steliou, K.; Chen, T. H. J. Am. Chem. Soc. 1978, 100, 1222. Harpp, D. N.; Ash, D. K. Int. J. Sulfur. Chem. A 1971, 1, 211. Harpp, D. N.; Ash, D. K. Int. J. Sulfur. Chem. A 1971, 1, 57.
68. Harpp, D. N. Studies in Organic Chemistry 28. Perspectives in The Organic Chemistry of Sulfur; Zwanenburg, B., Klunder, A. H., Eds.; Elsevier: Amsterdam, 1987. Harpp, D. N.; Steliou, K.; Chen, T. H. J. Am. Chem. Soc. 1978, 100, 1222. Harpp, D. N.; Ash, D. K. Int. J. Sulfur. Chem. A 1971, 1, 211. Harpp, D. N.; Ash, D. K. Int. J. Sulfur. Chem. A 1971, 1, 57.
69. Harpp, D. N. Studies in Organic Chemistry 28. Perspectives in The Organic Chemistry of Sulfur; Zwanenburg, B., Klunder, A. H., Eds.; Elsevier: Amsterdam, 1987. Harpp, D. N.; Steliou, K.; Chen, T. H. J. Am. Chem. Soc. 1978, 100, 1222. Harpp, D. N.; Ash, D. K. Int. J. Sulfur. Chem. A 1971, 1, 211. Harpp, D. N.; Ash, D. K. Int. J. Sulfur. Chem. A 1971, 1, 57.
70. Sullivan, A. B.; Boustany, K. Int. J. Sulfur. Chem. A 1971, 1, 207 . Mott, A. W.; Barany, G. Synthesis 1984, 657.
71. Sullivan, A. B.; Boustany, K. Int. J. Sulfur. Chem. A 1971, 1, 207 . Mott, A. W.; Barany, G. Synthesis 1984, 657.
72. McGahren, W. J.; Ding, W-D.; Ellestad, G. A. Disulfide Calicheamicins and the Chemistry of the Allylic Trisulfide group. Enediyne Antibiotics as Antitumor Agents; Borders, D. B., Doyle, T. W., Eds.; Dekker, Inc.: New York, 1995; Chapter 5, p 75.
73. i), (Miranda, E. I.; Diaz, M. J.; Rosado, I.; Soderquist, J. A. Tetrahedron Lett. 1994, 35, 3221) resulted in clean conversion into the protected sulfide xiii (45%). Exposure of xiii to HF/pyridine in the presence of the Harpp reagent (PhthNSSMe) gave the trisulfide 39 in low yield. Whereas, treatment of xiii with CsF/DMF resulted in clean formation of the disulfide 40 (70%). Presumably, in the latter process the thiolate xiv attacks the terminal sulfur atom with PhthNS-as the leaving group, and in the former reaction (HF/pyridine) the thiol displaces PhthN-. (Matrix Presented)
74. Lee, M. D. Identification, Isolation, and Structure Determination. Enediyne Antibiotics as Antitumor Agents; Borders, D. B., Doyle, T. W., Eds.; Dekker, Inc.: New York, 1995; Chapter 4, p 49.
75. Hallett, D. Unpublished results from this laboratory.
76. 2O and tetrahydrofuran were distilled from sodium benzophenone ketyl; dichloromethane and benzene were distilled from calcium hydride under argon.