Total synthesis of leustroducsin B via a convergent route

Tetrahedron Letters

Volumn 48, Issue 22, 2007, Pages 3829-3833

  Miyashita, Kazuyuki ^a,b   Tsunemi, Tomoyuki ^a   Hosokawa, Takafumi ^a   Ikejiri, Masahiro ^a   Imanishi, Takeshi ^a  

^a OSAKA UNIVERSITY   (Japan)

^b OSAKA OHTANI UNIVERSITY   (Japan)

Author keywords

Convergent route; Leustroducsin B; Proteinphosphatase inhibitor; Total synthesis

Indexed keywords

LEUSTRODUCSIN B; PROTEIN SERINE THREONINE KINASE INHIBITOR; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; DRUG SYNTHESIS; STILLE REACTION;

EID: 34247553744     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.03.152     Document Type: Article

References (52)

1. Kohama T., Enokita R., Okazaki T., Miyaoka H., Torikata A., Inukai M., Kaneko I., Kagasaki T., Sakaida Y., Satoh A., and Shiraishi A. J. Antibiot. 46 (1993) 1503
2. Kohama T., Nakamura T., Kinoshita T., Kaneko I., and Shiraishi A. J. Antibiot. 46 (1993) 1512
3. Kohama T., Katayama T., Inukai M., Maeda H., and Shiraishi A. Microbiol. Immunol. 38 (1994) 741
4. Koishi R., Yoshimura C., Kohama T., and Serizawa N. J. Interferon Cytokine Res. 22 (2002) 343
5. Kohama T., Maeda H., Imada Sakai J., Shiraishi A., and Yamashita K. J. Antibiot. 49 (1996) 91
6. Koishi R., Serizawa N., and Kohama T. J. Interferon Cytokine Res. 18 (1998) 863
7. Recent review:. Colby D.A., and Chamberlin A.R. Mini-Rev. Med. Chem. 6 (2006) 657
8. Ingebritsen T.S., and Cohen P. Eur. J. Biochem. 132 (1983) 255
9. Cohen P. Ann. Rev. Biochem. 58 (1989) 453
10. Walsh A.H., Cheng A., and Honkanen R.E. FEBS Lett. 416 (1997) 230
11. Kawada M., Kawatsu M., Masuda T., Ohba S., Amemiya M., Kohama T., Ishizuka M., and Takeuchi T. Int. Immunopharmacol. 3 (2003) 179
12. Lewy D.S., Gauss C.-M., Soenen D.R., and Boger D.L. Curr. Med. Chem. 9 (2002) 2005
13. Shibasaki M., and Kanai M. Heterocycles 66 (2005) 727
14. Boger D.L., Ichikawa S., and Zhong W. J. Am. Chem. Soc. 123 (2001) 4161
15. Cossy J., Pradaux F., and BouzBouz S. Org. Lett. 3 (2001) 2233
16. Chavez D.E., and Jacobsen E.N. Angew. Chem. 113 (2001) 3779
17. Angew. Chem., Int. Ed. 40 (2001) 3667
18. Reddy Y.K., and Falck J.R. Org. Lett. 4 (2002) 969
19. Esumi T., Okamoto N., and Hatakeyama S. Chem. Commun. (2002) 3042
20. Wang Y.-G., and Kobayashi Y. Org. Lett. 4 (2002) 4615
21. Fujii K., Maki K., Kanai M., and Shibasaki M. Org. Lett. 5 (2003) 733
22. Maki K., Motoki R., Fujii K., Kanai M., Kobayashi T., Tamura S., and Shibasaki M. J. Am. Chem. Soc. 127 (2005) 17111
23. Trost B.M., Frederiksen M.U., Papillon J.P.N., Harrington P.E., Shin S., and Shireman B.T. J. Am. Chem. Soc. 127 (2005) 3666
24. Yadav J.S., Prathap I., and Tadi B.P. Tetrahedron Lett. 47 (2006) 3773
25. Miyashita K., Ikejiri M., Kawasaki H., Maemura S., and Imanishi T. Chem. Commun. (2002) 742
26. Miyashita K., Ikejiri M., Kawasaki H., Maemura S., and Imanishi T. J. Am. Chem. Soc. 125 (2003) 8238
27. Structurally related natural products, phoslactomycins, were reported by Seto's group:. Fushimi S., Nishikawa S., Shimazu A., and Seto H. J. Antibiot. 42 (1989) 1019
28. Fushimi S., Furihata K., and Seto H. J. Antibiot. 42 (1989) 1026
29. Shimada K., Kaburagi Y., and Fukuyama T. J. Am. Chem. Soc. 125 (2003) 4048
30. Wang Y.-G., Takeyama R., and Kobayashi Y. Angew. Chem. 118 (2006) 3398
31. Angew. Chem., Int. Ed. 45 (2006) 3320
32. Pfenninger A. Synthesis (1986) 89
33. Katsuki T., and Martin V.S. Org. React. 48 (1996) 1-299
34. Recent review:. Blakemore P.R. J. Chem. Soc., Perkin Trans. 1 (2002) 2563
35. Kolb H.C., VanNieuwenhze M.S., and Sharpless K.B. Chem. Rev 94 (1994) 2483
36. Recent reviews:. Nicolaou K.C., Bulger P.G., and Sarlah D. Angew. Chem. 117 (2005) 4516
37. Angew. Chem., Int. Ed. 44 (2005) 4442
38. Li C.-J. Chem. Rev. 105 (2005) 3095
39. Espinet P., and Echavarren A.M. Angew. Chem. 116 (2004) 4808
40. Angew. Chem., Int. Ed. 43 (2004) 4704
41. Aerssens M.H.P., Van der Heiden R., Heus M., and Brandsma L. Synth. Commun. 20 (1990) 3421
42. Mitsunobu O. Synthesis (1981) 1
43. Valverde S., Bernabé M., Garcia-Ochoa S., and Gómez A.M. J. Org. Chem. 55 (1990) 2294
44. Mori K., Takigawa T., and Matsuo T. Tetrahedron 35 (1979) 933
45. Although some asymmetric Diels-Alder reactions for the preparation of the optically active cyclohexenecarboxylic acid 10 were reported, we utilized the optically active oxazolidinone:. Raw A.S., and Jang E.B. Tetrahedron 56 (2000) 3285
46. Linde II R.G., Egbertson M., Coleman R.S., Jones A.B., and Danishefsky S.J. J. Org. Chem. 55 (1990) 2771
47. Carboxylic acid 34 was prepared by oxidation of the corresponding optically active alcohol (94% ee) which was commercially available from Tokyo Chemical Industry Co., Ltd.
48. To the best of our knowledge, a similar epimerization was reported on the reaction of a sulfone derivative having a tetrahydrofuran ring:. Evans D.A., Rajapakse H.A., Chiu A., and Stenkamp D. Angew. Chem. 114 (2002) 4755
49. Angew. Chem., Int. Ed. 41 (2002) 4573
50. An olefinic by-product, which was produced by elimination of the neighboring MPM group, was obtained in 32% yield. Further optimization of this coupling reaction including utilization of other reactions is in progress, details of which would be described in a full article.
51. A mixture of the hydrated products, C-9 phosphate 48, C-8 phosphate 49 and cyclic phosphodiester 50, was obtained in 87% yield from 46, and the ratio was ca. 71:22:7, respectively. The mixture was employed for the next reaction without separation.{A figure is presented}
52. D +99.3 (c 0.0500, MeOH)].