An enantio- and diastereocontrolled synthesis of ()-7-deoxy-Trans-dihydronarciclasine

Heterocycles

Volumn 66, Issue 1, 2005, Pages 167-173

  Fujimura, Takashi ^a   Shibuya, Masatoshi ^a   Ogasawara, Kunio ^a   Iwabuchi, Yoshiharu ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33646868391     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/COM-05-S(K)68     Document Type: Article

References (67)

1. Hoshino O. In: Cordell G.A. (Ed). The Alkaloids Vol. 51 (1998), Academic Press, Inc., San Diego 181-236
2. For isolation and biological activities of pancratistatin, see; (a). Pettit G.R., Gaddamidi V., and Cragg G.M. J. Nat. Prod. 47 (1984) 1018
3. Pettit G.R., Gaddamidi V., Cragg G.M., Herald D.L., and Sagawa Y. J. Chem. Soc., Chem. Commun. (1984) 1693
4. For 7-deoxypancratistatin, see. Luduena R.F., Roach M.C., Prasad V., and Pettit G.R. Biochem. Pharmacol. 43 (1992) 539
5. For Narciclasine, see. Ghosal S., Singh S., Kumar Y., and Srivastava R.S. Phytochemisty 28 (1989) 611
6. Piozii F., Fuganti C., Mondelli R., and Ceriotti G. Tetrahedron 24 (1968) 1119
7. For lycoricidine, see. Okamoto T., Torii Y., and Isogai Y. Chem. Pharm. Bull. 16 (1968) 1860
8. For rans-dihydronarciclasine, see. Piozzi F., Marino M.L., Fuganti C., and Di Martino A. Phytochemistry 8 (1969) 1745
9. For 7-deoxy-trans-dihydronarciclasine, see. Pettit G.R., Cragg G.M., Singh S.B., Duke J.A., and Doubek D.L. J. Nat. Prod. 53 (1990) 176
10. Pettit G.R., Pettit III G.R., Backhaus R.A., Boyd M.R., and Meerow A.W. J. Nat. Prod. 56 (1993) 1682
11. Pettit G.R., Pettit III G.R., Groszek G., Backhaus R.A., Doubek D.L., Barr R.J., and Meerow A.W. J. Nat. Prod. 58 (1995) 756
12. Pettit G.R., Pettit III G.R., Backhaus R.A., and Boettner F.E. J. Nat. Prod. 58 (1995) 37
13. Pettit G.R., Gaddamidi V., Herald D.L., Singh S.B., Cragg G.M., Schmidt J.M., Boettner F.E., Williams M., and Sagawa Y. J. Nat. Prod. 49 (1986) 995
14. Kekre N., Griffin C., McNulty J., and Pandey S. Cancer Chemother. Pharmacol. 56 (2005) 29
15. Gabrielsen B., Monath T.P., Huggins J.W., Kefauver D.F., Pettit G.R., Groszek G., Hollingshead M., Kirsi J.J., Shannon W.M., Schubert E.M., DaRe J., Ugarkar B., Ussery M.A., and Phelan M.J. J. Nat. Prod. 55 (1992) 1569
16. Ouarzane-Amara M., Franetich J.-F., Mazier D., Pettit G.R., Meijer L., Doerig C., and Desportes-Livage I. Antimicrob. Agents Chemother 45 (2001) 3409
17. For an excellent review. Rinner U., and Hudlicky T. Synlett (2005) 365
18. For total synthesis of pancratistatin, see. Danishefsky S.J., and Lee J.Y. J. Am. Chem. Soc. 111 (1989) 4829
19. Tian X., Hudlicky T., and Königsberger K. J. Am. Chem. Soc. 117 (1995) 3634
20. Hudlicky T., Tian X., Königsberger K., Maurya R., Rouden J., and Fan B. J. Am. Chem. Soc. 118 (1996) 10752
21. Trost B.M., and Pulley S.R. J. Am. Chem. Soc. 117 (1995) 10143
22. Doyle T.J., Hendrix M., VanDerveer D., Javanmard S., and Haseltine J. Tetrahedron 52 (1997) 11153
23. Mugnus P., and Sebhat I.K. J. Am. Chem. Soc. 120 (1998) 5341
24. Magnus P., and Sebhat I.K. Tetrahedron 54 (1998) 15509
25. Rigby J.H., Maharoof U.S.M., and Mateo M.E. J. Am. Chem. Soc. 122 (2000) 6624
26. Pettit G.R., Melody N., and Herald D.L. J. Org. Chem. 66 (2001) 2583
27. Kim S., Ko H., Kim E., and Kim D. Org. Lett. 4 (2002) 1343
28. For total synthesis of narciclasine, see. Ko H., Kim E., Park J.E., Kim D., and Kim S. J. Org. Chem. 69 (2004) 112
29. Rigby J.H., and Mareo M.E. J. Am. Chem. Soc. 119 (1997) 12655
30. Gonzales D., Martinot T., and Hudlicky T. Tetrahedron Lett. 40 (1999) 3077
31. Keck G.E., Wager T.T., and Rodriques J.F.D. J. Am. Chem. Soc. 121 (1999) 5176
32. Rigby J.H., Maharoof U.S.M., and Mateo M.E. J. Am. Chem. Soc. 122 (2000) 6624
33. Elango S., and Yan T.-H. J. Org. Chem. 67 (2002) 6954
34. For recent synthetic approaches, see. Hudlicky T., Rinner U., Gonzalez D., Akgun H., Schilling S., Siengalewicz P., Martinot T.A., and G.R. P. J. Org. Chem. 67 (2002) 8726
35. McNulty J., Larichev V., and Pandey S. Bioorg. Med. Chem. Lett. 15 (2005) 5325
36. Manpadi M., and Kornienko A. Tetrahedron Lett. 46 (2005) 4433
37. Nadein O.N., and Kornienko A. Org. Lett. 6 (2004) 831
38. Rinner U., Hillebrenner H.L., Adams D.A., Hudlicky T., and Pettit G.R. Bioorg. Med. Chem. Lett. 14 (2004) 2911
39. Rinner U., Hudlicky T., Kwart L.D., and Fessner W.-D. Angew. Chem. Int. Ed. 43 (2004) 5342
40. Ibn-Ahmed S., Khaldi M., Chétien F., and Chapleur Y. J. Org. Chem. 69 (2004) 6722
41. Phung A.N., Zannetti M.T., Whited G., and Fessner W.-D. Angew. Chem. Int. Ed. 42 (2003) 4821
42. Elango S., and Yan T.-H. Tetrahedron 58 (2002) 7335
43. Elango S., and Yan T.-H. J. Org. Chem. 67 (2002) 6954
44. Takano S., Higashi Y., Kamikubo T., Moriya M., and Ogasawara K. Synthesis (1993) 948
45. Konno H., and Ogasawara K. Synthesis (1999) 1135
46. Ogasawara K. Pure Appl. Chem. 66 (1994) 2119
47. Ogasawara K. J. Syn. Org. Chem., Jpn. 57 (1999) 957
48. For total synthesis of ()-7-deoxy-trans-dihydronarciclasine, see (a). Chida N., Jitsuoka M., Yamamoto Y., Ohtsuka M., and Ogawa S. For the total synthesis of racemic 7-deoxy-trans-dihydronarciclasine, see (b). Heterocycles 43 (1996) 1385
49. For the conversion of natural lycoricidine into 7-deoxy-rans-narciclasine, see. Isobe K., Taga J., and Tsuda Y. Heterocycles 9 (1978) 625
50. Gabrielsen B., Monath T.P., Huggins J.W., Kefauver D.F., Pettit G.P., Groszek G., Hollingshead M., Kirshi J.J., Shannon W.M., Schubert E.M., DaRe J., Ugarkar B., Ussery M.A., and Phelan M.J. J. Nat. Prod. 55 (1992) 1569
51. Banwell M.G., Bissett B.D., Busato S., Cowden C.J., Hockless D.C., Holman J.W., Read R.W., and Wu A.W. J. Chem. Soc., Chem. Commun. (1995) 2551
52. Johnson C.R., Adams J.P., Braun M.P., and Senanayaka C.B.W. Tetrahedron Lett. 33 (1992) 917
53. Nicolaou K.C., Sato M., Miller N.D., Gunzner J.L., Renaud J., and Untersteller E. Angew. Chem., Int. Ed. Eng. 35 (1996) 889
54. Miyaura N., and Suzuki A. Chem. Rev. 95 (1995) 2457
55. Prepared from 1-bromo-(3,4-methylenedioxy)benzene via lithiation using t-BuLi and subsequent
56. Iguchi S., Nakai H., and Hayashi M. J. Org. Chem. 44 (1979) 1363
57. Lal B., Pramanik B.N., Manhas M.S., and Bose A.K. Tetrahedron Lett. (1977) 1997
58. Chen S.-H., Farina V., Vyas D.M., Doyle T.W., Long B.H., and Fairchild C. J. Org. Chem. 61 (1996) 2065
59. N2′ selective nature of the allylic system in 13 prompted us to switch the chirality of the starting material for obtaining natural 7-deoxy-trans-dihydronarciclasine.
60. N2′ selectivity in Mitsunobu reaction of allylic alcohols: (a). Mitsunobu O. Synthesis (1981) 1
61. Sobti A., and Sulikowski G.A. Tetrahedron Lett. 35 (1994) 3661
62. Mulzer J., and Funk G. Synthesis (1995) 101
63. Shull B.K., Sasai T., Nichols J.B., and Koreeda M. J. Org. Chem. 62 (1997) 8294
64. Takano S., Moriya M., Higashi Y., and Ogasawara K. J. Chem. Soc., Chem. Commun. (1993) 177
65. Honzumi M., Hiroya K., Taniguchi T., and Ogasawara K. Chem. Commun. (1999) 1985
66. The use of a benzoyl protecting group afforded a 3≠1 diasteomixture under the same conditions.
67. Robins M.J., Lewandowska E., and Wnuk S.F. J. Org. Chem. 63 (1998) 7375