Efficient synthesis of (±)-γ-lycorane employing stereoselective conjugate addition to nitroolefin

Tetrahedron Letters

Volumn 45, Issue 15, 2004, Pages 3043-3045

  Yasuhara, Tomohisa ^a   Osafune, Emi ^a   Nishimura, Katsumi ^b   Yamashita, Mitsuaki ^b   Yamada, Ken Ichi ^b   Muraoka, Osamu ^a   Tomioka, Kiyoshi ^b  

^a KINKI UNIVERSITY   (Japan)

^b KYOTO UNIVERSITY   (Japan)

Author keywords

Addition; Alkaloid; Nitroolefin; Synthesis

Indexed keywords

ALKALOID DERIVATIVE; ALKENE DERIVATIVE; GAMMA LYCORANE; LITHIUM DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; ASYMMETRIC SYNTHESIS; CONJUGATION; CYCLIZATION; CYCLOADDITION; DRUG SYNTHESIS; MICHAEL ADDITION; MITSUNOBU REACTION; STEREOCHEMISTRY; SYNTHESIS;

EID: 1642400497     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.02.096     Document Type: Article

References (63)

1. Martin S.F. Brossi A. The Alkaloids. vol. 30:1987;251-376 Academic, New York.
2. Grundon M.F. Nat. Prod. Rep. 6:1989;79-84.
3. Lewis J.R. Nat. Prod. Rep. 11:1995;339-345.
4. Hoshino O. Cordell G.A. The Alkaloids. vol. 51:1998;323-424 Academic, San Diego.
5. Yui S., Mikami M., Kitahara M., Yamazaki M. Immunopharmacology. 40:1998;151-162.
6. Review on asymmetric Michael additions to nitroalkenes: Berner O.M., Tedeschi L., Enders D. Eur. J. Org. Chem. 2002;1877-1894.
7. External ligand controlled asymmetric reactions: Tomioka K. Synthesis. 1990;541-549.
8. Recent example: Yamashita M., Yamada K., Tomioka K. J. Am. Chem. Soc. 126:2004;. 1954-1955.
9. Takeda K., Kotera K., Mizukami S., Kobayashi M. Chem. Pharm. Bull. 8:1960;483-486.
10. Kotera K. Tetrahedron. 12:1961;240-247.
11. Kotera K. Tetrahedron. 12:1961;248-261.
12. Tsuda Y., Isobe K. J. Synth. Org. Chem. Jpn. 34:1976;625-640.
13. Yasuhara T., Nishimura K., Yamashita M., Fukuyama N., Yamada K., Muraoka O., Tomioka K. Org. Lett. 5:2003;1123-1126.
14. Synthesis of 3 : Ueda N., Tokuyama T., Sakan T. Bull. Chem. Soc. Jpn. 39:1966;2012-2014.
15. Ganem B. Tetrahedron Lett. 1971;4105-4108.
16. Umezawa B., Hoshino O., Sawaki S., Sato S., Numao N. J. Org. Chem. 42:1977;4272-4275.
17. Iida H., Yuasa Y., Kibayashi C. J. Org. Chem. 44:1979;1074-1080.
18. Higashiyama H., Honda T., Otomasu H., Kametani T. Planta Med. 48:1983;268-271.
19. Sugiyama N., Narimiya M., Iida H., Kikuchi T. J. Hetelocycl. Chem. 25:1988;1455-1457.
20. Baeckvall J.E., Anderson P.G., Stone G.B., Gogoll A. J. Org. Chem. 56:1991;2988-2993.
21. Pearson W.H., Schkeryantz J.M. J. Org. Chem. 57:1992;6783-6789.
22. Grotjahn D.B., Vollhardt K.P.C. Synthesis. 1993;567-605.
23. Banwell M.G., Wu A.W. J. Chem. Soc. Perkin Trans. 1. 1994;2671-2672.
24. Yoshizaki H., Satoh H., Sato T., Nukui S., Shibasaki M., Mori M. J. Org. Chem. 60:1995;2016-2021.
25. Angle S.R., Boyce J.P. Tetrahedron Lett. 36:1995;6185-6188.
26. Ikeda M., Ohtani S., Sato T., Ishibashi H. Synthesis. 1998;1925-1933.
27. Cossy J., Tresnard L., Pardo D.G. Tetrahedron Lett. 40:1999;1125-1128.
28. Cossy J., Tresnard L., Pardo D.G. Eur. J. Org. Chem. 1999;1925-1933.
29. Magnus P., Bailey J.M., Porter M.J. Tetrahedron. 55:1999;13927-13936.
30. Hoang-Cong X., Quiclet-Sire B., Zard S.Z. Tetrahedron Lett. 40:1999;2125-2126.
31. Cassayre J., Zart S.Z. Synlett. 1999;501-503.
32. Banwell M.G., Harvey J.E., Hockless D.C.R., Wu A.W. J. Org. Chem. 65:2000;4241-4250.
33. Padwa A., Brodney M.A., Lynch S.M. J. Org. Chem. 66:2001;1716-1724.
34. Tamura O., Matsukida H., Toyao A., Takeda Y., Ishibashi H. J. Org. Chem. 67:2002;5537-5545.
35. Shao Z., Chen J., Huang R., Wang C., Li L., Zhang H. Synlett. 2003;2228-2230.
36. Denmark S.E., Senanayake B.W. J. Org. Chem. 58:1993;1835-1858.
37. Application of the reported protocols for asymmetric nitro-aldol reaction would give an optically active 5 : Davis A.P., Dempsey K.J. Tetrahedron: Asymmetry. 6:1995;2829-2840.
38. Sasai H., Tokunaga T., Watanabe S., Suzuki T., Itoh N., Shibasaki M. J. Org. Chem. 60:1995;7388-7389.
39. Sasai H., Arai S., Tahara Y., Shibasaki M. J. Org. Chem. 60:1995;6656-6657.
40. Magnus P., Pye P. Chem. Commun. 1995;1933-1934.
41. Iseki K., Oishi S., Sasai H., Shibasaki M. Tetrahedron Lett. 37:1996;9081-9084.
42. Hanessian S., Devasthale P.V. Bioorg. Med. Chem. Lett. 6:1996;2201-2206.
43. Oshida J., Okamoto M., Azuma S., Tanaka T. Tetrahedron: Asymmetry. 8:1997;2579-2584.
44. Takaoka E., Yoshikawa N., Yamada Y.M.A., Sasai H., Shibasaki M. Heterocycles. 46:1997;157-163.
45. Menzel A., Ohrlein R., Griesser H., Wehner V., Jager V. Synthesis. 1999;1691-1702.
46. Knudsen K.R., Risgaard T., Nishiwaki N., Gothelf K.V., Jorgensen K.A. J. Am. Chem. Soc. 123:2001;5843-5844.
47. Davis A.V., Driffield M., Smith D.K. Org. Lett. 3:2001;3075-3078.
48. Yukihiro M., Matsumoto K. Angew. Chem., Int. Ed. 41:2002;1031-1033.
49. Tian J., Yamagiwa N., Matsunaga S., Shibasaki M. Angew. Chem., Int. Ed. 41:2002;3636-3638.
50. Sasai H., Watanabe S., Suzuki T., Shibasaki M. Org. Synth. 78:2002;14-22.
51. Ooi T., Doda K., Maruoka K. J. Am. Chem. Soc. 125:2003;2054-2055.
52. Corey E.J., Zhang F.-Y. Org. Lett. 2:2000;4257-4259.
53. Although the possibility of thermodynamic control is not excluded, attempted epimerization of a nitro group (NaOMe in MeOH) recovered 11.
54. Melton J., McMurry J.E. J. Org. Chem. 40:1975;2138-2139.
55. Ballini R., Palestini C. Tetrahedron Lett. 35:1994;5731-5734.
56. Mitsunobu O. Synthesis. 1981;1-28.
57. Prange T., Rodríguez M.S., Suárez E. J. Org. Chem. 68:2003;4422-4431.
58. 2) at δ 5.01 are 4.0 and 4.1 Hz, indicating all-cis arrangement of three substituents in 11.
59. Johnson F. Chem. Rev. 68:1968;375-413.
60. Tomioka K. J. Synth. Org. Chem. Jpn. 51:1993;1116-1123.
61. Castello A., Jaime C., Marquet J., Moreno-Manas M. Tetrahedron. 41:1985;3791-3802.
62. Michaelides M.R., Hong Y., DiDomenico S. Jr., Bayburt E.K., Asin K.E., Britton D.R., Lin C.W., Shiosaki K. J. Med. Chem. 40:1997;1585-1599.
63. 8c.