Asymmetric total synthesis of (+)-phoslactomycin B

Organic Letters

Volumn 10, Issue 11, 2008, Pages 2139-2142

  Shibahara, Setsuya ^a   Fujino, Masataka ^a   Tashiro, Yasumasa ^a   Takahashi, Keisuke ^a   Ishihara, Jun ^a   Hatakeyama, Susumi ^a  

^a NAGASAKI UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

LACTONE; ORGANOPHOSPHORUS COMPOUND; PHOSLACTOMYCIN B;

ARTICLE; CHEMISTRY; ENZYME SPECIFICITY; STEREOISOMERISM; SYNTHESIS;

LACTONES; ORGANOPHOSPHORUS COMPOUNDS; STEREOISOMERISM; SUBSTRATE SPECIFICITY;

EID: 52649178941     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol8004672     Document Type: Article

References (56)

1. (a) Fushimi, S.; Nishikawa, S.; Shimizu, A.; Seto, H. J. Antibiot. 1989, 42, 1019-1025.
2. (b) Fushimi, S.; Furihata, K.; Seto, H. J. Antibiot. 1989, 42, 1026-1036.
3. (c) Ozasa, T.; Suzuki, K.; Sasamata, M.; Tanaka, K.; Kobori, M.; Kadota, S.; Nagai, K.; Saito, T.; Watanabe, S.; Iwanami, M. J. Antibiot. 1989, 42, 1331-1338.
4. (d) Ozasa, T.; Tanaka, K.; Sasamata, M.; Kaniwa, H.; Shimizu, M.; Matsumoto, H.; Iwanami, M. J. Antibiot. 1989, 42, 1339-1343.
5. (e) Shibata, T.; Kurihara, S.; Yoda, K.; Haruyama, H. Tetrahedron 1995, 51, 11999-12012.
6. (f) Sekiyama, Y.; Palaniappan, N.; Reynolds, K. A.; Osada, H. Tetrahedron 2003, 59, 7465-7471.
7. (g) Choudhuri, S. D.; Ayers, S.; Soine, W. H.; Reynolds, K. V. J. Antibiot. 2005, 58, 573-582.
8. (h) Mizuhara, N.; Usuki, Y.; Ogita, M.; Fujita, K.; Kuroda, M.; Doe, M.; Iio, H.; Tanaka, T. J. Antibiot. 2007, 60, 762-765.
9. Tomiya, T.; Uramoto, M.; Isono, K. J. Antibiot. 1990, 43, 118-121.
10. (a) Kohma, 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, 1503-1511.
11. (b) Kohma, T.; Nakamura, T.; Kinoshita, T.; Kaneko, I.; Shiraishi, A. J. Antibiot. 1993, 46, 1512-1519.
12. (a) Lewy, D. S.; Gauss, C.-M.; Soenen, D. R.; Boger, D. L. Curr. Med. Chem. 2002, 9, 2005-2032.
13. (b) 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, 15694-15695.
14. (a) Walsh, A. H.; Cheng, A.; Honkanen, R. E. FEBS Lett. 1997, 416, 230-234.
15. (b) Hastie, C. J.; Cohen, P. T. FEBS Lett. 1998, 431, 357-361.
16. (c) Kawada, M.; Kawatsu, M.; Masuda, T.; Ohba, S.; Amemiya, M.; Kohama, T.; Ishizuka, M.; Takeuuchi, T. Int. Immunopharmacol. 2003, 3, 179-188.
17. (d) Teruya, T.; Shimizu, S.; Kanoh, N.; Osada, H. FEBS Lett. 2005, 579, 2463-2468.
18. (a) An acyloxy moiety on the cyclohexane ring, the only structural variation seen in these phosphate esters, does not affect the PP2A-specific inhibitory activity. Usui, T.; Marriott, G.; Inagaki, M.; Swarup, G.; Osada, H. J. Biochem. 1999, 125, 960-965.
19. Palaniappan, N.; Kim, B. S.; Sekiyama, Y.; Osada, H.; Reynolds, K. A. J. Biol. Chem. 2003, 278, 35552-35557.
20. For reviews, see: Shibasaki, M.; Kanai, M. Heterocycles 2005, 66, 727-741.
21. (a) Boger, D. L.; Ichikawa, S.; Zhong, W. J. Am. Chem. Soc. 2001, 123, 4161-4167.
22. (b) Cossy, J.; Pradaux, F.; BouzBouz, S. Org. Lett. 2001, 3, 2233-2235.
23. (c) Chavez, D. E.; Jacobsen, E. N. Angew. Chem., Int. Ed. 2001, 40, 3667-3670.
24. (d) Reddy, Y. K.; Falck, J. R. Org. Lett. 2002, 4, 961-971.
25. (e) Miyashita, K.; Ikejiri, M.; Kawasaki, H.; Maemura, S.; Imanishi, T. Chem. Commun. 2002, 742-743.
26. (f) Esumi, T.; Okamoto, N.; Hatakeyama, S. Chem. Commun. 2002, 3042-3043.
27. (g) Wang, Y.-G.; Kobayashi, Y. Org. Lett. 2002, 4, 4615-4618.
28. (h) Miyashita, K.; Ikejiri, M.; Kawasaki, H.; Maemura, S.; Imanishi, T. J. Am. Chem. Soc. 2003, 125, 8238-8243.
29. (i) Fujii, K.; Maki, K.; Kanai, M.; Shibasaki, M. Org. Lett. 2003, 5, 733-736.
30. (j) Maki, K.; Motoki, R.; Fujii, K.; Kanai, M.; Kobayashi, T.; Tamura, S.; Shibasaki, M. J. Am. Chem. Soc. 2005, 127, 17111-17117.
31. (k) Trost, B. M.; Frederiksen, M. U.; Papillon, J. P. N.; Harrington, P. E.; Shin, S.; Shireman, B. T. J. Am. Chem. Soc. 2005, 127, 3666-3667.
32. (l) Hayashi, Y.; Yamaguchi, H.; Toyoshima, M.; Okado, K.; Toyo, T.; Shoji, M. Org. Lett. 2008, 10, 1405-1408.
33. (m) Yadav, J. S.; Prathap, I.; Tadai, B. P. Tetrahedron Lett. 2006, 47, 3773-3776.
34. Shimada, K.; Kabburagi, Y.; Fukuyama, T. J. Am. Chem. Soc. 2003, 125, 4048-4049. The first synthesis was achieved in 0.07% overall yield in 47 steps exclusive of the manipulation on the cyclohexane ring.
35. Miyashita, K.; Tsunemi, T.; Hosokawa, T.; Ikejiri, M.; Imanishi, T. Tetrahedron Lett. 2007, 48, 3829-33833. The convergent synthesis required 33 total steps exclusive of the manipulation on the cyclohexane ring. The overall yield of the longest linear sequence was 0.32% in 24 steps.
36. Wang, Y.-G.; Takeyama, T.; Kobayashi, Y. Angew. Chem., Int. Ed. 2006, 45, 3320-3323. The first synthesis was achieved in 0.61% overall yield in 40 steps exclusive of the manipulation on the cyclohexane ring.
37. For reviews, see: Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457-2483.
38. (b) Suzuki, A. J. Organomet. Chem. 1999, 576, 147-168.
39. For a review, see: Deiters, A.; Martin, S. F. Chem. Rev. 2004, 104, 2199-2238.
40. For a review, see: Kolb, H. C.; VanNieuwenhze, M. S.; Sharpless, K. B. Chem. Rev. 1994, 94, 2483-2547.
41. Brown, H. C.; Bhat, K. S. J. Am. Chem. Soc. 1986, 108, 293-294.
42. Roush, W. R.; Ando, K.; Powers, D. B.; Palkowitz, A. D.; Halterman, R. L. J. Am. Chem. Soc. 1990, 112, 6339-6348.
43. (a) Braun, N. A.; Klein, I.; Spitzner, D.; Vogler, B.; Braun, S.; Borrmann, H.; Simon, A. Liebigs Ann. 1995, 2165-2169.
44. (b) Moreau, X.; Campagne, J.-M. J. Org. Chem. 2003, 68, 5346-5350.
45. Kamatani, A.; Overman, L. E. J. Org. Chem. 1999, 64, 8743-8744.
46. Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413-4450.
47. Nicolaou, K. C.; Yue, E. W.; Naniwa, Y.; Riccardis, F. D.; Nadin, A.; Leresche, J. E.; Greca, S. L.; Yang, Z. Angew. Chem., Int. Ed. 1994, 33, 2187-2190.
48. Dihydroxylation employing AD-mix-β turned out to be unsatisfactory in terms of reproducibility.
49. This phenomenon was also proved by the enantiomeric purity of the recovered 17 (59% ee).
50. Rodriguez, A.; Nomen, M.; Spur, B. W.; Godfroid, J. J. Tetrahedron Lett. 1999, 40, 5161-5164.
51. Taniguchi, M.; Kobayashi, S.; Nakagawa, M.; Hino, T.; Kishi, Y. Tetrahedron Lett. 1986, 27, 4763-4766.
52. Evans, D. A.; Chapman, K. T.; Carreira, E. M. J. Am. Chem. Soc. 1988, 110, 3560-3578.
53. Chen, K.-M.; Hardtmann, E.; Prasad, K.; Repic, O.; Shapiro, M. J. Tetrahedron Lett. 1987, 28, 155-158.
54. Stille, J. K.; Groh, B. L. J. Am. Chem. Soc. 1987, 109, 813-817.
55. 3SnCl, THF, -78 °C; (ii) CpZrHCl, THF.
56. Exposure of 30 to the desilylation conditions over 3 h caused appreciable decomposition of 32. The optimal procedure to obtain 32 involves a 2 h reaction of 30 and another 2 h reaction of 31 formed together with 32 in the first desilylation (see the Supporting Information).