Structure elucidation and synthesis of the lignans from the seeds of Hernandia ovigera L.

Studies in Natural Products Chemistry

Volumn 18, Issue PART K, 1995, Pages 551-606

  Arimoto, Masao ^a   Yamaguchi, H ^a   Nishibe, S ^a  

^a NONE

Author keywords

[No Author keywords available]

Indexed keywords

EID: 77957060692     PISSN: 15725995     EISSN: None     Source Type: Book Series    
DOI: 10.1016/S1572-5995(96)80034-2     Document Type: Chapter

References (124)

1. R.D. Haworth J. Chem. Soc. 1942 448
2. R.D. Haworth Nature (London) 147 1941 225
3. a) R.S. Ward Chem. Soc. Rev. 11 1982 75
4. b) D.A. Whiting Nat Prod. Reports 2 1985 191
5. D.A. Whiting Nat Prod. Reports 4 1987 499
6. c) D.C. Ayres J.D. Loike Lignans 1990 Cambridge University Press
7. a) T. Hata Nippon Kagakukaishi 63 1942 1540
8. b) H. Furukawa F. Ueda M. Ito K. Ito H. Ishii J. Haginiwa Yakugaku Zasshi 92 1972 150
9. C. Nishino T. Mitsui Tetrahedron Lett. 1973 335
10. H. Yamaguchi M. Arimoto K. Yamamoto A. Numata Yakugaku Zasshi 99 1979 674
11. K. Noguchi M. Kanan Yakugaku Zasshi 60 1940 629
12. J.L. Hartwell A.W. Schrecher J.M. Johnson J. Am. Chem. Soc. 75 1953 2138
13. J.L. Hartwell A.W. Schrecher J. Am. Chem. Soc. 76 1954 4034
14. A.W. Schrecher J.L. Hartwell J. Am. Chem. Soc. 75 1953 5916
15. P.B. Mcdoniel J.R. Cole J. Pharm. Sci. 61 1972 1992
16. M. Kuhn A. von Warburg Helv. Chim. Acta 67 1967 1546
17. H. Yamaguchi M. Arimoto M. Tanoguchi T. Ishida M. Inoue Chem. Pharm. Bull. 30 1982 3212
18. M. Tanoguchi M. Arimoto H. Saika H. Yamaguchi Chem. Pharm. Bull. 35 1987 4162
19. S. Nishibe S. Hisada I. Inagaki Yakugaku Zasshi 94 1974 522
20. J. Harmatha M. Budesinsky A. Trka Collect. Czech. Chem. Commun. 47 1982 644
21. M. Kozawa N. Morita K. Hata Yakugaku Zasshi 98 1978 1486
22. H. Erdtman J. Harmatha Phytochemistry 18 1979 1495
23. S.K. Koul S.C. Taneja K.L. Dhar C.K. Atal Phytochemistry 22 1983 999
24. L.P. Badheka B.R. Prabhu N.B. Mulchandani Phytochemistry 25 1986 487
25. P. Richomme J. Bruneton P. Cabalion M.M. Debray J. Nat. Prod. 47 1984 879
26. M.-C. Chalandre C. Pareyre J. Bruneton Ann. Pharm. Fr. 42 1984 317
27. P. Richomme J. Bruneton A. Cave Heterocycles 23 1985 309
28. K. Tomioka H. Mizuguchi K. Koga Chem. Pharm. Bull. 30 1982 4304
29. M. Tanoguchi E. Hosono M. Kitaoka M. Arimoto H. Yamaguchi Chem. Pharm. Bull. 39 1991 1873
30. D. Takaoka N. Takamatsu Y. Saheki K. Kono C. Nakaoka H. Hiroi Nippon Kagaku Kaishi 1975 2192
31. W.M. Kamil P.M. Dewick Phytochemistry 25 1986 2093
32. P. Richomme J. Bruneton A. Cave Heterocycles 23 1985 309
33. H. Yamaguchi M. Arimoto M. Tanoguchi A. Numata Yakugaku Zasshi 101 1981 485
34. W.J. Gensler F. Johnson A.D.B. Sloan J. Am. Chem. Soc. 82 1960 6074
35. H. Kofod C.J. Ørgensen Acta, Chem. Scand. 8 1954 1296
36. L. Fa S. Tianmin F. Fengyong Yao Hsueh Hsueh Pao 14 1979 241
37. C. Xingrue H. Zhibi Z. Guangfang Yao Hsueh Hsueh Pao 15 1980 158
38. H.P. Plaumann J.G. Smith R. Rodrigo J. Chem. Soc., Chem. Commun. 1980 354
39. B.J. Arnold S.M. Mellows P.G. Sammes J. Chem. Soc., Perkin Trans. 1 1973 1266
40. A.S. Kende M.L. King D.P. Curran J. Org. Chem. 46 1981 2826
41. J.E.T. Corrie G.H. Green E. Ritchie W.C. Taylor Aust. J. Chem. 23 1970 133
42. E. Wenkert H.E. Gottlieb O.R. Gottlieb M.O.S. Pereira M.D. Formiga Phytochemistry 15 1976 1547
43. A. Bax J. Magn Reson. 53 1983 517
44. D. Takaoka M. Imooka M. Hiroi Bull. Chem. Soc. Jpn. 50 1977 2821
45. S. Nisibe K. Okabe S. Hisada Chem. Pharm. Bull. 29 1981 2078
46. L.P. Badheka B.R. Prabhu N.B. Mulchandani Phytochemistry 25 1986 487
47. S.K. Koul S.C. Taneja K.L. Dhar C.K. Atal Phytochemistry 23 1984 2099
48. B.R. Prabhu N.B. Mulchandani Phytochemistry 24 1985 329
49. M. Tanoguchi T. Kashima H. saika T. Inoue M. Arimoto H. Yamaguchi Chem. Pharm. Bull. 37 1989 68
50. a) D.N. Kirk L.M. McLaughlin A.M. Lawson K.D.R. Setchell S.K. Patel J. Chem. Soc., Perkin Trans. 1 1985 35
51. b) A. Pelter R.S. Ward P. Satyanarayana P. Collins J. Chem. Soc., Perkin Trans. 1983 643
52. c) Y. Landais J.-P. Robin Tetrahedron Lett. 27 1986 1785
53. M. Kato Y. Hayashi T. Miwa T. Sakan Nippon Kagaku Zasshi 85 1964 225
54. a) J.L. Hartwell W.E. Detty J. Am. Chem. Soc. 72 1950 246
55. b) J.L. Hartwell A.W. Schrecher G.Y. Greeberg J. Am. Chem. Soc. 74 1952 6285
56. c) E. Bianchi K. Sheth J.R. Cole Tetrahedron Lett. 1969 2759
57. A.M. Duffield J. Heterocycl. Chem. 4 1967 16
58. A. Pelter J. Chem. Soc. (C) 1968 74
59. T. Gilchrist R. Hodges L. Porte J. Chem. Soc. 1962 1780
60. L.H. Klemm K.W. Gopinath D. Hsu Lee F.W. Kelly E. Trod T.M. McGuuire Tetrahedron 22 1966 1797
61. a) Z. Horii M. Tsujiuchi T. Momose Tetrahedron Lett. 1969 1079
62. Z. Horii K. Ohkawa S. Kim T. Momose Chem. Pharm. Bull. 16 1968 2404
63. Z. Horii K. Ohkawa S. Kim T. Momose J. Chem. Soc., Chem. Commun. 1968 653
64. b) M. Okigawa T. Maeda N. Kawano Tetrahedron 26 1970 4301
65. a) W. Klyne R. Stevenson R.J. Swan J. Chem. Soc. (C) 1966 893
66. R.J. Swan W. Klyne H. MacLean Can. J. Chem. 45 1967 319
67. b) J. Sakakibara H. Ina M. Yasue Yakugaku Zasshi 94 1974 1377
68. a) R.B. Bates J.B. Wood J. Org. Chem. 37 1972 562
69. b) T.J. Petcher H.P. Weber M. Kuhn A. Von Warzburg J. Chem. Soc., Perkin Trans. 2 1973 288
70. G. Germain P. Main M.M. Woolfson Acta Crystallogr., Sect. A 27 1971 368
71. International Tables for X-ray-Crystallography Vol. IV 1974 Kynoch Press Birmingham
72. The Universal Crystallographic Computing System 1979 Library of Programs, Osaka University, Computing Center
73. a) S. Takano S. Otaki K. Ogasawara Heterocycles 23 1985 2811
74. b) A.R. Beard M.G.B. Drew J. Mann L.T.F. Wong Tetrahedron 43 1987 4207
75. a) T. Ishiguro H. Mizuguchi K. Tomioka K. Koga Chem. Pharm. Bull. 33 1985 609
76. b) K. Tomioka K. Koga Tetrahedron Lett. 1979 3315
77. Y. Landais A. Lebrun V. Lenain J.-P. Robin Tetrahedron Lett. 28 1987 5161
78. W.J. Gensler C.M. Samour S.Y. Wang F. Johnson J. Am. Chem. Soc. 82 1960 1714
79. G.A. Olah R. Malhotra S.C. Narang J.A. Olah Synthesis 1978 672
80. K. Shimizu S. Fukushima Yakugaku zasshi 87 1967 1079
81. T. Kurihara M. Kikuchi S. Suzuki S. Hisamitsu Yakugaku Zasshi 98 1978 1586
82. L.H. Klemm K.W. Gopinath G.C. Karaboyas G.L. Capp D.H. Lee Tetrahedron 20 1964 871
83. B.A. McKittrick R. Stevenson J. Chem. Soc., Perkin Trans. 1 1984 709
84. J. Villieras M. Rambaud Synthesis 1983 300
85. K. Holmberg B. Hansen Acta Chem. Scand., Ser. B 33 1979 410
86. B.S. Joshi N. Viswanathan V. Balakrishnan D.H. Gawad K.R. Ravindranath Tetrahedron 35 1979 1665
87. a) H.M. Thompson J. Org. Chem. 36 1971 2577
88. b) H.M. Thompson R.E. Naipawer J. Org. Chem. 37 1972 1307
89. V.N. Aiyar F.C. Chang J. Org. Chem. 40 1975 2384
90. P.A. Ganeshpure R. Stevenson J. Chem. Soc., perkin Trans. 1 1981 1681
91. T. Kashima M. Tanoguchi M. Arimoto H. Yamaguchi Chem. Pharm. Bull. 39 1991 192
92. T. Morimoto M. Chiba K. Achiwa Tetrahedron Lett. 31 1990 261
93. E. Spath F. Wessely L. Kornferd Chem. Ber. 65 1932 1536
94. R.D. Haworth T. Richardson J. Chem. Soc. 1936 348
95. E. Schreier Helv. Chim. Acta 46 1963 75
96. E. Schreier Helv. Chim. Acta 47 1964 1529
97. Y. Ikeya H. Taguchi I. Yoshioka Chem. Pharm. Bull. 27 1979 2536
98. S. Ghosal S. Banerjee J. Chem. Soc., Chem. Commun. 1979 165
99. S. Ghosal R.P.S. Chauhan R.S. Srivastava Phytochemistry 13 1974 2281
100. H. Yamaguchi S. Nakajima M. Arimoto M. Tanoguchi T. Ishida M. Inoue Chem. Pharm. Bull. 32 1984 1754
101. H. Koford C.J. Ørgensen Acta Chem. Scand. 9 1955 1327
102. a) J.H. Clark H.L. Holland J.M. Miller Tetrahedron Lett. 1976 3361
103. b) H. Ishii E. Kawanabe N. Fukasaku T. Yokoshima M. Akasu Chem. Pharm. Bull. 30 1982 2761
104. D.J. Sam H.E. Simmons J. Am. Chem. Soc. 96 1974 2252
105. N.J. Lewis S.Y. Gabhe M.R. DeLaMater J. Org. Chem. 42 1977 1479
106. R.D. Rieke S.E. Bales J. Am. Chem. Soc. 96 1974 1775
107. R.G.R. Bacon S.C. Rennison J. Chem. Soc., (C) 1969 312
108. R.G.R. Bacon J.R. Wright J. Chem. Soc., (C) 1969 1978
109. P. Buck G. Kobrich Tetrahedron Lett. 1967 1563
110. P. Wiriyachitra M.P. Cava J. Org. Chem. 42 1977 2274
111. H. Yamaguchi M. Arimoto S. Nakajima M. Tanoguchi Y. Fukada Chem. Pharm. Bull. 34 1986 2056
112. a) J.L. Hartwell A.W. Schrecker J. Am. Chem. Soc. 73 1951 2909
113. b) D.C. Ayres C.K. Lim J. Chem. Soc., Perkin Trans. 1 1972 1350
114. W.J. Gensler F. Johnson A.D.B. Sloan J. Am. Chem. Soc. 82 1960 6074
115. W.J. Gensler F. Johnson J. Am. Chem. Soc. 85 1963 3670
116. V.N. Aiyar F.C. Chang J. Org. Chem. 42 1977 246
117. E.J. Corey J.W. Suggs Tetrahedron Lett. 1975 2647
118. V. BaZant M. Capca M. Cerny V. Chvalovsky K. Kochloefi M. Kraus J. Malek Tetrahedron Lett. 1968 3303
119. T. Nakata T. Tanaka T. Oishi Tetrahedron Lett. 24 1981 2653
120. A. Kende M.L. King D.P. Curran J. Org. Chem. 46 1981 2826
121. F.C. Chang Synthetic Commun. 11 1981 875
122. B.L. Allwood H.S. Zavareh J.F. Stoddart D.J. Williams J. Chem. Soc., Chem. Commun. 1984 1461
123. S. Nishibe M. Chiba A. Sakushima S. Hisada S. Yamanouchi M. Takido U. Sankawa A. Sakakibara Chem. Pharm. Bull. 28 1980 850
124. K. Yamasaki K. Fujita Chem. Pharm. Bull. 27 1979 43