Total synthesis and evaluation of phostriecin and key structural analogues

Journal of Organic Chemistry

Volumn 75, Issue 22, 2010, Pages 7505-7513

  Burke, Christopher P ^a   Swingle, Mark R ^b   Honkanen, Richard E ^b   Boger, Dale L ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

^b UNIVERSITY OF SOUTH ALABAMA COLLEGE OF MEDICINE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ABSOLUTE STEREOCHEMISTRY; ANTI-TUMOR ACTIVITIES; MECHANISM OF ACTION; MONOESTERS; NATURAL PRODUCTS; PROTEIN PHOSPHATASE 2A; SELECTIVE INHIBITORS; STRUCTURAL ANALOGUE; SYNTHETIC ANALOGUES; TOTAL SYNTHESIS;

STEREOCHEMISTRY;

5 [(TERT BUTYLDIPHENYLSILYL)OXY] 6 [6 [(TERT BUTYLDIPHENYLSILYL)OXY] 4 HYDROXY 5 METHYLHEPTADEC 1 EN 1 YL] 5,6 DIHYDRO 2H PYRAN 2 ONE; 6 [(TERT BUTYLDIMETHYLSILYL)OXY] 2 [4 (1 ETHOXYETHOXY) 6 HYDROXY 5 METHYLHEPTADEC 1 EN 1 YL] 3,6 DIHYDRO 2H PYRAN 3 YL PIVALATE; ALCOHOL; ALPHA,BETA UNSATURATED LACTONE; BIS[(9H FLUOREN 9 YL)METHYL] [[(TERT BUTYLDIPHENYLSILYL)OXY] 1 [3 [(TERT BUTYLDIPHENYLSILYL)OXY]6 OXO 3,6 DIHYDRO 2H PYRAN 2 YL] 5 METHYLHEPTADEC 1 EN 4 YL]PHOSPHATE; LACTONE DERIVATIVE; NATURAL PRODUCT; PHOSPHATE; PHOSPHATE MONOESTER; PHOSPHOPROTEIN PHOSPHATASE; PHOSPHOPROTEIN PHOSPHATASE INHIBITOR; PHOSTRIECIN; SODIUM 6 HYDROXY 1 [3 HYDROXY 6 OXO 3,6 DIHYDRO 2H PYRAN 2 YL] 5 METHYLHEPTADEC 1 EN 4 YL HYDROGEN PHOSPHATE; SULFATE; SULTRIECIN; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME ACTIVITY; HYDROPHOBICITY; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; STRUCTURE ANALYSIS;

ALKENES; ALKYNES; ANTINEOPLASTIC AGENTS; HUMANS; LACTONES; ORGANOPHOSPHATES; PROTEIN PHOSPHATASE 2; STEREOISOMERISM;

EID: 78449265566     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo1010203     Document Type: Article

References (68)

1. Swingle, M.; Ni, L.; Honkanen, R. E. Methods Mol. Biol. 2007, 365, 23
2. Virshup, D. M.; Shenolikar, S. Mol. Cell 2009, 33, 537
3. McConnell, J. L; Wadzinski, B. E. Mol. Pharmacol. 2009, 75, 1249
4. Ohkuma, H.; Naruse, N.; Nishiyama, Y.; Tsuno, T.; Hoshino, Y.; Sawada, Y.; Konishi, M.; Oki, T. J. Antibiot. 1992, 45, 1239
5. Lewy, D. S.; Gauss, C.-M.; Soenen, D. R.; Boger, D. L. Curr. Med. Chem. 2002, 9, 2005
6. Isolation: Tunac, J. B.; Graham, B. D.; Dobson, W. E. J. Antibiot. 1983, 36, 1595
7. Stampwala, S. S.; Bunge, R. H.; Hurley, T. R.; Willmer, N. E.; Brankiewicz, A. J.; Steinman, C. E.; Smitka, T. A.; French, J. C. J. Antibiot. 1983, 36, 1601 Total syntheses: Boger, D. L.; Ichikawa, S.; Zhong, W. J. Am. Chem. Soc. 2001, 123, 4161
8. Chavez, D. E.; Jacobsen, E. N. Angew. Chem., Int. Ed. 2001, 40, 3667
9. Reddy, Y. K.; Falck, J. R. Org. Lett. 2002, 4, 969
10. Miyashita, K.; Ikejiri, M.; Kawasaki, H.; Maemura, S.; Imanishi, T. Chem. Commun. 2002, 742
11. Miyashita, K.; Ikejiri, M.; Kawasaki, H.; Maemura, S.; Imanishi, T. J. Am. Chem. Soc. 2003, 125, 8238
12. Esumi, T.; Okamoto, N.; Hatakeyama, S. Chem. Commun. 2002, 3042
13. Fujii, K.; Maki, K.; Kanai, M.; Shibasaki, M. Org. Lett. 2003, 5, 733
14. Trost, B. M.; Frederiksen, M. U.; Papillon, J. P.; Harrington, P. E.; Shin, S.; Shireman, B. T. J. Am. Chem. Soc. 2005, 127, 3666
15. Maki, K.; Motoki, R.; Fujii, K.; Kanai, M.; Kobayashi, T.; Tamura, S.; Shibasaki, M. J. Am. Chem. Soc. 2005, 127, 17111
16. Yadav, J. S.; Prathap, I.; Tadi, B. P. Tetrahedron Lett. 2006, 47, 3773
17. Hayashi, Y.; Yamaguchi, H.; Toyoshima, M.; Okado, K.; Toyo, T.; Shoji, M. Org. Lett. 2008, 10, 1405
18. Sarkar, S. M.; Wanzala, E. N.; Shibahara, S.; Takahashi, K.; Ishihara, J.; Hatakeyama, S. Chem. Commun. 2009, 5907
19. Robles, O.; McDonald, F. E. Org. Lett. 2009, 11, 5498
20. Boger, D. L.; Hikota, M.; Lewis, B. M. J. Org. Chem. 1997, 62, 1748
21. Hokanson, G. C.; French, J. C. J. Org. Chem. 1985, 50, 462
22. Buck, S. B.; Hardouin, C.; Ichikawa, S.; Soenen, D. R.; Gauss, C.-M.; Hwang, I.; Swingle, M. R.; Bonness, K. M.; Honkanen, R. E.; Boger, D. L. J. Am. Chem. Soc. 2003, 125, 15694
23. Swingle, M. B.; Amable, L.; Lawhorn, B. G.; Buck, S. B.; Burke, C. P.; Ratti, P.; Fisher, K. L.; Boger, D. L.; Honkanen, R. E. J. Pharmacol. Exp. Ther. 2009, 331, 45
24. Takeuchi, T.; Takahashi, N.; Ishi, K.; Kusayanagi, T.; Kuramochi, K.; Sugawara, F. Bioorg. Med. Chem. 2009, 17, 8113
25. Isolation: Amemiya, M.; Someno, T.; Sawa, R.; Naganawa, H.; Ishizuka, M.; Takeuchi, T. J. Antibiot. 1994, 47, 541
26. Amemiya, M.; Ueno, M.; Osono, M.; Masuda, T.; Kinoshita, N.; Nishida, C.; Hamada, M.; Ishizuka, M.; Takeuchi, T. J. Antibiot. 1994, 47, 536 Total syntheses: Lawhorn, B. G.; Boga, S. B.; Wolkenberg, S. E.; Colby, D. A.; Gauss, C.-M.; Swingle, M. R.; Amable, L.; Honkanen, R. E.; Boger, D. L. J. Am. Chem. Soc. 2006, 128, 16720
27. Lawhorn, B. G.; Boga, S. B.; Wolkenberg, S. E.; Boger, D. L. Heterocycles 2006, 70, 65
28. Bialy, L.; Waldmann, H. Chem.-Eur. J. 2004, 10, 2759
29. Bialy, L.; Waldmann, H. Angew. Chem., Int. Ed. 2002, 41, 1748
30. Jung, W.-H.; Guyenne, S; Riesco-Fagundo, C.; Mancuso, J.; Nakamura, S.; Curran, D. P. Angew. Chem., Int. Ed. 2008, 47, 1130
31. Isolation: Ozasa, T.; Tanaka, K.; Sasamata, M.; Kaniwa, H.; Shimizu, M.; Matsumoto, H.; Iwanami, M. J. Antibiot. 1989, 42, 1339 Total syntheses: Wang, Y.-G.; Takeyama, R.; Kobayashi, Y. Angew. Chem., Int. Ed. 2006, 45, 3320
32. Shibahara, S.; Fujino, M.; Tashiro, Y.; Takahashi, K.; Ishihara, J.; Hatakeyama, S. Org. Lett. 2008, 10, 2139
33. Isolation: Kohama, T.; Enokita, R.; Okazaki, T.; Miyaoka, H.; Torikata, A.; Inukai, M.; Kaneko, I.; Kagasaki, T.; Sakaida, Y.; Satoh, A.; Shiraishi, A. J. Antibiot. 1993, 46, 1503
34. Kohama, T.; Nakamura, T.; Kinoshita, T.; Kaneko, I.; Shiraishi, A. J. Antibiot. 1993, 46, 1512 Total syntheses: Matsuhashi, H.; Shimada, K. Tetrahedron 2002, 58, 5619
35. Shimada, K.; Kaburagi, Y.; Fukuyama, T. J. Am. Chem. Soc. 2003, 125, 4048
36. Miyashita, K.; Tsunemi, T.; Hosokawa, T.; Ikejiri, M.; Imanishi, T. J. Org. Chem. 2008, 73, 5360
37. Isolation: Fushimi, S.; Nishikawa, S.; Shimazu, A.; Seto, H. J. Antibiot. 1989, 42, 1019 Total synthesis: König, C. M.; Gebhardt, B.; Schleth, C.; Dauber, M.; Koert, U. Org. Lett. 2009, 11, 2728
38. Burke, C. P.; Haq, N.; Boger, D. L. J. Am. Chem. Soc. 2010, 132, 2157
39. Yang, Z.-C.; Jiang, X.-B.; Wang, Z.-M.; Zhou, W.-S. J. Chem. Soc., Perkin Trans. 1 1997, 317
40. Racherla, U. S.; Brown, H. C. J. Org. Chem. 1991, 56, 401
41. Nicolaou, K. C.; Patron, A. P.; Ajito, K.; Richter, P. K.; Khatuya, H.; Bertinato, P.; Miller, R. A.; Tomaszewski, M. J. Chem.-Eur. J. 1996, 2, 847
42. Oppolzer, W.; Radinov, R. N. Helv. Chim. Acta 1992, 75, 170
43. Trost, B. M.; Weiss, A. H.; von Wangelin, A. J. J. Am. Chem. Soc. 2006, 128, 8
44. Takita, R.; Yakura, K.; Oshima, T.; Shibasaki, M. J. Am. Chem. Soc. 2005, 127, 13760
45. Frantz, D. E.; Fässler, R.; Carreira, E. M. J. Am. Chem. Soc. 2000, 122, 1806
46. Noyori, R.; Ohta, M.; Hsiao, Y.; Kitamura, M.; Ohta, T.; Takaya, H. J. Am. Chem. Soc. 1986, 108, 7117
47. Noyori, R.; Ohkuma, T.; Kitamura, H.; Takaya, H.; Sayo, H.; Kumobayashi, S.; Akutagawa, S. J. Am. Chem. Soc. 1987, 109, 5856
48. Noyori, R.; Tomino, I.; Tanimoto, Y.; Nishizawa, M. J. Am. Chem. Soc. 1984, 106, 6709
49. Noyori, R.; Tomino, I.; Yamada, M.; Nishizawa, M. J. Am. Chem. Soc. 1984, 106, 6717
50. Corey, E. J.; Fuchs, P. L. Tetrahedron Lett. 1972, 13, 3769
51. Ramirez, F.; Desai, N. B.; McKelvie, N. J. Am. Chem. Soc. 1962, 84, 1745
52. Tohda, Y.; Sonogashira, K.; Hagihara, N. Synthesis 1977, 777
53. Corey, E. J.; Bakshi, R. K.; Shibata, S. J. Am. Chem. Soc. 1987, 109, 5551
54. Corey, E. J.; Katzenellenbogen, J. A.; Posner, G. H. J. Am. Chem. Soc. 1967, 89, 4245
55. Georgiadis, M. P.; Couladouros, E. A. J. Org. Chem. 1986, 51, 2725
56. Babu, R. S.; Zhou, M.; O'Doherty, G. A. J. Am. Chem. Soc. 2004, 126, 3428
57. Hakimelahi, G. H.; Proba, Z. A.; Ogilvie, K. K. Tetrahedron Lett. 1981, 22, 4775
58. Mitsunobu, O. Synthesis 1981, 1
59. Dess, D. B.; Martin, J. C. J. Am. Chem. Soc. 1991, 113, 7277
60. Belosludtsev, Y. Y.; Borer, B. C.; Taylor, R. J. K. Synthesis 1991, 320
61. Uenishi, J.; Kawahama, R.; Yonemitsu, O.; Tsuji, J. J. Org. Chem. 1998, 63, 8965
62. Still, W. C.; Schneider, J. A. Tetrahedron Lett. 1980, 21, 1035
63. 1H NMR data for "desulfated" 1 were reported; however, these data alone were not sufficient to confirm that it and triol 35 share the same structure. See ref 2.
64. Rychnovsky, S. D.; Skalitzky, D. J. Tetrahedron Lett. 1990, 31, 945
65. Evans, D. A.; Rieger, D. L.; Gage, J. R. Tetrahedron Lett. 1990, 31, 7099
66. Commercially available from Bioaustralis.
67. Sheidt, K. A.; Chen, H.; Follows, B. C.; Chemler, S. R.; Coffey, D. S.; Roush, W. R. J. Org. Chem. 1998, 63, 6436
68. De Jong, R. S.; Mulder, N. H.; Uges, D. R. A.; Sleijfer, D. Th.; Hoppener, F. J. P.; Groen, H. J. M.; Willemse, P. H. B.; Van der Graf, W. T. A.; De Vries, E. G. E. Br. J. Cancer 1999, 79, 882