-
2
-
-
1042289535
-
-
ed. by J. E. Saxton, Supplement, Wiley, Chichester
-
R. B. Herbert, in "Monoterpenoid Indole Alkaloids", ed. by J. E. Saxton, Supplement, Wiley, Chichester, 1994, pp. 1-13. See also, R. B. Herbert, The Biosynthesis of Secondary Metabolites, 2nd Ed., Chapman and Hall, London, 1989, pp. 168-170.
-
(1994)
Monoterpenoid Indole Alkaloids
, pp. 1-13
-
-
Herbert, R.B.1
-
3
-
-
0345652268
-
-
Chapman and Hall, London
-
R. B. Herbert, in "Monoterpenoid Indole Alkaloids", ed. by J. E. Saxton, Supplement, Wiley, Chichester, 1994, pp. 1-13. See also, R. B. Herbert, The Biosynthesis of Secondary Metabolites, 2nd Ed., Chapman and Hall, London, 1989, pp. 168-170.
-
(1989)
The Biosynthesis of Secondary Metabolites, 2nd Ed.
, pp. 168-170
-
-
Herbert, R.B.1
-
4
-
-
0342588200
-
-
ed. by J. E. Saxton, Supplement, Wiley, Chichester
-
M. Lounasmaa and A. Tolvanen, in "Monoterpenoid Indole Alkaloids", ed. by J. E. Saxton, Supplement, Wiley, Chichester, 1994, pp. 57-159.
-
(1994)
Monoterpenoid Indole Alkaloids
, pp. 57-159
-
-
Lounasmaa, M.1
Tolvanen, A.2
-
5
-
-
0003873379
-
-
Technique et Documentation - Lavoisier, Paris
-
J Bruneton, Pharmacognosie, Phytochimie, Plantes médicinales, 2nd Ed., Technique et Documentation - Lavoisier, Paris, 1993, pp. 821-822.
-
(1993)
Pharmacognosie, Phytochimie, Plantes Médicinales, 2nd Ed.
, pp. 821-822
-
-
Bruneton, J.1
-
6
-
-
0013008795
-
-
H. Rapoport, R. J. Windgassen, Jr., N. A. Hughes, and T. P. Onak, J. Am. Chem. Soc., 1960, 82, 4404. See also, H. Rapoport, R. J. Windgassen, N. A. Hughes, and T. P. Onak, J. Am. Chem. Soc., 1959, 81, 3166.
-
(1960)
J. Am. Chem. Soc.
, vol.82
, pp. 4404
-
-
Rapoport, H.1
Windgassen R.J., Jr.2
Hughes, N.A.3
Onak, T.P.4
-
7
-
-
0343893809
-
-
H. Rapoport, R. J. Windgassen, Jr., N. A. Hughes, and T. P. Onak, J. Am. Chem. Soc., 1960, 82, 4404. See also, H. Rapoport, R. J. Windgassen, N. A. Hughes, and T. P. Onak, J. Am. Chem. Soc., 1959, 81, 3166.
-
(1959)
J. Am. Chem. Soc.
, vol.81
, pp. 3166
-
-
Rapoport, H.1
Windgassen, R.J.2
Hughes, N.A.3
Onak, T.P.4
-
8
-
-
0001238850
-
-
M-M. Janot, Tetrahedron, 1961, 14, 113. See also, F. Puisieux, R. Goutarel, M.-M. Janot, and A. Le Hir, C. R. Acad. Sci., Paris, 1959, 249, 1369.
-
(1961)
Tetrahedron
, vol.14
, pp. 113
-
-
Janot, M.-M.1
-
9
-
-
0001238850
-
-
M-M. Janot, Tetrahedron, 1961, 14, 113. See also, F. Puisieux, R. Goutarel, M.-M. Janot, and A. Le Hir, C. R. Acad. Sci., Paris, 1959, 249, 1369.
-
(1959)
C. R. Acad. Sci., Paris
, vol.249
, pp. 1369
-
-
Puisieux, F.1
Goutarel, R.2
Janot, M.-M.3
Le Hir, A.4
-
10
-
-
0343022461
-
-
A. Chatterjee, A. Banerji, P. Majumder, and R. Majumder, Bull. Chem. Soc. Japan, 1976, 49, 2000.
-
(1976)
Bull. Chem. Soc. Japan
, vol.49
, pp. 2000
-
-
Chatterjee, A.1
Banerji, A.2
Majumder, P.3
Majumder, R.4
-
11
-
-
0344357820
-
-
note
-
We prefer in the present work to use the stereodescriptor E for clarity and uniformity, even though geissoschizine (2) and geissoschizine methyl ether (22) are genuine natural products.
-
-
-
-
12
-
-
0001672403
-
-
E. E. van Tamelen, J. P. Yardley, M. Miyano, and W. B. Hinshaw, Jr., J. Am. Chem. Soc., 1969, 91, 7349.
-
(1969)
J. Am. Chem. Soc.
, vol.91
, pp. 7349
-
-
Van Tamelen, E.E.1
Yardley, J.P.2
Miyano, M.3
Hinshaw W.B., Jr.4
-
13
-
-
84982076462
-
-
G. Rackur and E. Winterfeldt, Chem. Ber., 1976, 109, 3837. See also, G. Höfle, P. Heinstein, J. Stöckigt, and M. H. Zenk, Planta Medica, 1980, 40, 120.
-
(1976)
Chem. Ber.
, vol.109
, pp. 3837
-
-
Rackur, G.1
Winterfeldt, E.2
-
14
-
-
0019293472
-
-
G. Rackur and E. Winterfeldt, Chem. Ber., 1976, 109, 3837. See also, G. Höfle, P. Heinstein, J. Stöckigt, and M. H. Zenk, Planta Medica, 1980, 40, 120.
-
(1980)
Planta Medica
, vol.40
, pp. 120
-
-
Höfle, G.1
Heinstein, P.2
Stöckigt, J.3
Zenk, M.H.4
-
15
-
-
0043255820
-
-
M. Damak, A. Ahond, P. Potier, and M.-M. Janot, Tetrahedron Lett., 1976, 4731. See also, A. Chiaroni, C. Riche, M. Païs, and R. Goutarel, Tetrahedron Lett., 1976, 4729 and R. Goutarel, M. Païs, H. E. Gottlieb, and E. Wenkert, Tetrahedron Lett., 1978, 1235.
-
(1976)
Tetrahedron Lett.
, pp. 4731
-
-
Damak, M.1
Ahond, A.2
Potier, P.3
Janot, M.-M.4
-
16
-
-
0345652243
-
-
M. Damak, A. Ahond, P. Potier, and M.-M. Janot, Tetrahedron Lett., 1976, 4731. See also, A. Chiaroni, C. Riche, M. Païs, and R. Goutarel, Tetrahedron Lett., 1976, 4729 and R. Goutarel, M. Païs, H. E. Gottlieb, and E. Wenkert, Tetrahedron Lett., 1978, 1235.
-
(1976)
Tetrahedron Lett.
, pp. 4729
-
-
Chiaroni, A.1
Riche, C.2
Païs, M.3
Goutarel, R.4
-
17
-
-
0042754657
-
-
M. Damak, A. Ahond, P. Potier, and M.-M. Janot, Tetrahedron Lett., 1976, 4731. See also, A. Chiaroni, C. Riche, M. Païs, and R. Goutarel, Tetrahedron Lett., 1976, 4729 and R. Goutarel, M. Païs, H. E. Gottlieb, and E. Wenkert, Tetrahedron Lett., 1978, 1235.
-
(1978)
Tetrahedron Lett.
, pp. 1235
-
-
Goutarel, R.1
Païs, M.2
Gottlieb, H.E.3
Wenkert, E.4
-
18
-
-
0026467132
-
-
H. Takayama, T. Watanabe, H. Seki, N. Aimi, and S. Sakai, Tetrahedron Lett., 1992, 33, 6831.
-
(1992)
Tetrahedron Lett.
, vol.33
, pp. 6831
-
-
Takayama, H.1
Watanabe, T.2
Seki, H.3
Aimi, N.4
Sakai, S.5
-
19
-
-
0345652242
-
-
note
-
In order to make uniform and clarify the conformational presentation of compounds C(3)Hα-C(15)Hα and C(3)Hβ-C(15)Hα compounds, we present the latter compounds (trans relationship) as C(3)Hα-C(15)Hβ compounds, even though in most naturally occurring examples C(15)H is α.
-
-
-
-
20
-
-
0344789655
-
-
note
-
13C NMR shift value of C-6 (the most characteristic one for the conformational examination of compounds of the present type) is mentioned in the text. Other shift values are given in the formulae. Readers interested in details are referred to the original papers mentioned in the text.
-
-
-
-
21
-
-
0028210891
-
-
B. Tirkkonen, J. Miettinen, J. Salo, R. Jokela, and M. Lounasmaa, Tetrahedron, 1994, 50, 3537.
-
(1994)
Tetrahedron
, vol.50
, pp. 3537
-
-
Tirkkonen, B.1
Miettinen, J.2
Salo, J.3
Jokela, R.4
Lounasmaa, M.5
-
22
-
-
0022412603
-
-
C. Bohlmann, R. Bohlmann, E. Guitian Rivera, C. Vogel, M. D. Manandhar, and E. Winterfeldt, Liebigs Ann. Chem., 1985, 1752.
-
(1985)
Liebigs Ann. Chem.
, pp. 1752
-
-
Bohlmann, C.1
Bohlmann, R.2
Guitian Rivera, E.3
Vogel, C.4
Manandhar, M.D.5
Winterfeldt, E.6
-
24
-
-
0010669561
-
-
M. Lounasmaa, R. Jokela, B. Tirkkonen, and T. Tamminen, Tetrahedron, 1989, 45, 7615.
-
(1989)
Tetrahedron
, vol.45
, pp. 7615
-
-
Lounasmaa, M.1
Jokela, R.2
Tirkkonen, B.3
Tamminen, T.4
-
25
-
-
0001754737
-
-
M. Lounasmaa, R. Jokela, J. Miettinen, and M. Halonen, Heterocycles, 1992, 34, 1497.
-
(1992)
Heterocycles
, vol.34
, pp. 1497
-
-
Lounasmaa, M.1
Jokela, R.2
Miettinen, J.3
Halonen, M.4
-
26
-
-
0000608134
-
-
M. Lounasmaa, R. Jokela, B. Tirkkonen, J. Miettinen, and M. Halonen, Heterocycles, 1992, 34, 321. See also, F. E. Ziegler and J. G. Sweeny, Tetrahedron Lett., 1969, 1097.
-
(1992)
Heterocycles
, vol.34
, pp. 321
-
-
Lounasmaa, M.1
Jokela, R.2
Tirkkonen, B.3
Miettinen, J.4
Halonen, M.5
-
27
-
-
0013596357
-
-
M. Lounasmaa, R. Jokela, B. Tirkkonen, J. Miettinen, and M. Halonen, Heterocycles, 1992, 34, 321. See also, F. E. Ziegler and J. G. Sweeny, Tetrahedron Lett., 1969, 1097.
-
(1969)
Tetrahedron Lett.
, pp. 1097
-
-
Ziegler, F.E.1
Sweeny, J.G.2
-
28
-
-
0027408263
-
-
R. Jokela, M. Halonen, and M. Lounasmaa, Tetrahedron, 1993, 49, 2567.
-
(1993)
Tetrahedron
, vol.49
, pp. 2567
-
-
Jokela, R.1
Halonen, M.2
Lounasmaa, M.3
-
29
-
-
0027965813
-
-
M. Lounasmaa, R. Jokela, P. Hanhinen, J. Miettinen, and J. Salo, Tetrahedron, 1994, 50, 9207.
-
(1994)
Tetrahedron
, vol.50
, pp. 9207
-
-
Lounasmaa, M.1
Jokela, R.2
Hanhinen, P.3
Miettinen, J.4
Salo, J.5
-
30
-
-
0028866618
-
-
M. Lounasmaa, R. Jokela, C. Laine, and P. Hanhinen, Tetrahedron Lett., 1995, 36, 8687.
-
(1995)
Tetrahedron Lett.
, vol.36
, pp. 8687
-
-
Lounasmaa, M.1
Jokela, R.2
Laine, C.3
Hanhinen, P.4
-
31
-
-
0029068616
-
-
M. Lounasmaa, P. Hanhinen, and R. Jokela, Tetrahedron, 1995, 51, 8623.
-
(1995)
Tetrahedron
, vol.51
, pp. 8623
-
-
Lounasmaa, M.1
Hanhinen, P.2
Jokela, R.3
-
32
-
-
0029932476
-
-
M. Lounasmaa, R. Jokela, U. Anttila, P. Hanhinen, and C. Laine, Tetrahedron, 1996, 52, 6803.
-
(1996)
Tetrahedron
, vol.52
, pp. 6803
-
-
Lounasmaa, M.1
Jokela, R.2
Anttila, U.3
Hanhinen, P.4
Laine, C.5
-
33
-
-
0001626765
-
-
M. Lounasmaa, R. Jokela, P. Hanhinen, C. Laine, and U. Anttila, Heterocycles, 1996, 43, 1699.
-
(1996)
Heterocycles
, vol.43
, pp. 1699
-
-
Lounasmaa, M.1
Jokela, R.2
Hanhinen, P.3
Laine, C.4
Anttila, U.5
-
36
-
-
0010483826
-
-
M. Lounasmaa and M. Hämeilä, Tetrahedron, 1978, 34, 437. See also, M. Lounasmaa and C.-J. Johansson, Tetrahedron, 1977, 33, 113, M. Lounasmaa, H. Merikallio, and M. Puhakka, Tetrahedron, 1978, 34, 2995, and M. Lounasmaa and T. Tamminen, Tetrahedron, 1991, 47, 2879.
-
(1978)
Tetrahedron
, vol.34
, pp. 437
-
-
Lounasmaa, M.1
Hämeilä, M.2
-
37
-
-
0001023433
-
-
M. Lounasmaa and M. Hämeilä, Tetrahedron, 1978, 34, 437. See also, M. Lounasmaa and C.-J. Johansson, Tetrahedron, 1977, 33, 113, M. Lounasmaa, H. Merikallio, and M. Puhakka, Tetrahedron, 1978, 34, 2995, and M. Lounasmaa and T. Tamminen, Tetrahedron, 1991, 47, 2879.
-
(1977)
Tetrahedron
, vol.33
, pp. 113
-
-
Lounasmaa, M.1
Johansson, C.-J.2
-
38
-
-
0005185879
-
-
M. Lounasmaa and M. Hämeilä, Tetrahedron, 1978, 34, 437. See also, M. Lounasmaa and C.-J. Johansson, Tetrahedron, 1977, 33, 113, M. Lounasmaa, H. Merikallio, and M. Puhakka, Tetrahedron, 1978, 34, 2995, and M. Lounasmaa and T. Tamminen, Tetrahedron, 1991, 47, 2879.
-
(1978)
Tetrahedron
, vol.34
, pp. 2995
-
-
Lounasmaa, M.1
Merikallio, H.2
Puhakka, M.3
-
39
-
-
0026090739
-
-
M. Lounasmaa and M. Hämeilä, Tetrahedron, 1978, 34, 437. See also, M. Lounasmaa and C.-J. Johansson, Tetrahedron, 1977, 33, 113, M. Lounasmaa, H. Merikallio, and M. Puhakka, Tetrahedron, 1978, 34, 2995, and M. Lounasmaa and T. Tamminen, Tetrahedron, 1991, 47, 2879.
-
(1991)
Tetrahedron
, vol.47
, pp. 2879
-
-
Lounasmaa, M.1
Tamminen, T.2
-
40
-
-
33745418501
-
-
The C-10 and C-11 shifts given for compound (25)(32 in Ref. 30) have to be interchanged
-
E. Wenkert, J. S. Bindra, C.-J. Chang, D. W. Cochran, and F. M. Schell, Acc. Chem. Res., 1974, 7, 46. The C-10 and C-11 shifts given for compound (25)(32 in Ref. 30) have to be interchanged.
-
(1974)
Acc. Chem. Res.
, vol.7
, pp. 46
-
-
Wenkert, E.1
Bindra, J.S.2
Chang, C.-J.3
Cochran, D.W.4
Schell, F.M.5
-
41
-
-
0000208494
-
-
G. W. Gribble, R. B. Nelson, J. L. Johnson, and G. C. Levy, J. Org. Chem., 1975, 40, 3720. See also, G. W. Gribble and R. B. Nelson, J. Org. Chem., 1973, 38, 2831.
-
(1975)
J. Org. Chem.
, vol.40
, pp. 3720
-
-
Gribble, G.W.1
Nelson, R.B.2
Johnson, J.L.3
Levy, G.C.4
-
42
-
-
84989107635
-
-
G. W. Gribble, R. B. Nelson, J. L. Johnson, and G. C. Levy, J. Org. Chem., 1975, 40, 3720. See also, G. W. Gribble and R. B. Nelson, J. Org. Chem., 1973, 38, 2831.
-
(1973)
J. Org. Chem.
, vol.38
, pp. 2831
-
-
Gribble, G.W.1
Nelson, R.B.2
-
44
-
-
33947297495
-
-
J. D. Roberts, F. J. Weigert, J. I. Kroschwitz, and H. J. Reich, J. Am. Chem. Soc., 1970, 92, 1338.
-
(1970)
J. Am. Chem. Soc.
, vol.92
, pp. 1338
-
-
Roberts, J.D.1
Weigert, F.J.2
Kroschwitz, J.I.3
Reich, H.J.4
-
45
-
-
0000757081
-
-
I. Ninomiya, T. Naito, O. Miyata, T. Shinada, E. Winterfeld, R. Freund, and T. Ishida, Heterocycles, 1990, 30, 1031. See also, T. Naito, T. Shinada, O. Miyata, I. Ninomiya, and T. Ishida, Heterocycles, 1988, 27, 1603 and R. Freund and E. Winterfeldt, Liebigs Ann. Chem., 1988, 1007.
-
(1990)
Heterocycles
, vol.30
, pp. 1031
-
-
Ninomiya, I.1
Naito, T.2
Miyata, O.3
Shinada, T.4
Winterfeld, E.5
Freund, R.6
Ishida, T.7
-
46
-
-
0345220440
-
-
I. Ninomiya, T. Naito, O. Miyata, T. Shinada, E. Winterfeld, R. Freund, and T. Ishida, Heterocycles, 1990, 30, 1031. See also, T. Naito, T. Shinada, O. Miyata, I. Ninomiya, and T. Ishida, Heterocycles, 1988, 27, 1603 and R. Freund and E. Winterfeldt, Liebigs Ann. Chem., 1988, 1007.
-
(1988)
Heterocycles
, vol.27
, pp. 1603
-
-
Naito, T.1
Shinada, T.2
Miyata, O.3
Ninomiya, I.4
Ishida, T.5
-
47
-
-
84985180858
-
-
I. Ninomiya, T. Naito, O. Miyata, T. Shinada, E. Winterfeld, R. Freund, and T. Ishida, Heterocycles, 1990, 30, 1031. See also, T. Naito, T. Shinada, O. Miyata, I. Ninomiya, and T. Ishida, Heterocycles, 1988, 27, 1603 and R. Freund and E. Winterfeldt, Liebigs Ann. Chem., 1988, 1007.
-
(1988)
Liebigs Ann. Chem.
, pp. 1007
-
-
Freund, R.1
Winterfeldt, E.2
-
49
-
-
0024513739
-
-
E. Wenkert, M. Guo, M. Pestchanker, Y.-J. Shi, and Y. Vankar, J. Org. Chem., 1989, 54, 1166. See also, E. Wenkert, Y. D. Vankar, and J. S. Yadav, J. Am. Chem. Soc., 1980, 102, 7971 and V. B. Birman and V. H. Rawal, Tetrahedron Lett., 1998, 39, 7219.
-
(1989)
J. Org. Chem.
, vol.54
, pp. 1166
-
-
Wenkert, E.1
Guo, M.2
Pestchanker, M.3
Shi, Y.-J.4
Vankar, Y.5
-
50
-
-
0019136158
-
-
E. Wenkert, M. Guo, M. Pestchanker, Y.-J. Shi, and Y. Vankar, J. Org. Chem., 1989, 54, 1166. See also, E. Wenkert, Y. D. Vankar, and J. S. Yadav, J. Am. Chem. Soc., 1980, 102, 7971 and V. B. Birman and V. H. Rawal, Tetrahedron Lett., 1998, 39, 7219.
-
(1980)
J. Am. Chem. Soc.
, vol.102
, pp. 7971
-
-
Wenkert, E.1
Vankar, Y.D.2
Yadav, J.S.3
-
51
-
-
0032192164
-
-
E. Wenkert, M. Guo, M. Pestchanker, Y.-J. Shi, and Y. Vankar, J. Org. Chem., 1989, 54, 1166. See also, E. Wenkert, Y. D. Vankar, and J. S. Yadav, J. Am. Chem. Soc., 1980, 102, 7971 and V. B. Birman and V. H. Rawal, Tetrahedron Lett., 1998, 39, 7219.
-
(1998)
Tetrahedron Lett.
, vol.39
, pp. 7219
-
-
Birman, V.B.1
Rawal, V.H.2
-
52
-
-
0345652240
-
-
note
-
2O: 296.1890. Found: 296.1912.
-
-
-
-
53
-
-
0014222237
-
-
N. J. Dastoor, A. A. Gorman, and H. Schmidt, Helv. Chim. Acta, 1967, 50, 213.
-
(1967)
Helv. Chim. Acta
, vol.50
, pp. 213
-
-
Dastoor, N.J.1
Gorman, A.A.2
Schmidt, H.3
-
54
-
-
0344789651
-
-
note
-
2O: 296.1890. Found: 296.1906.
-
-
-
-
55
-
-
0344789650
-
-
C. Kan, S.-K. Kan, M. Lounasmaa, and H.-P. Husson, Acta Chem. Scand., 1981, 35B, 269.
-
(1981)
Acta Chem. Scand.
, vol.35 B
, pp. 269
-
-
Kan, C.1
Kan, S.-K.2
Lounasmaa, M.3
Husson, H.-P.4
-
56
-
-
0028961258
-
-
M. Lounasmaa, R. Jokela, P. Hanhinen, J. Miettinen, and J. Salo, J. Nat. Prod., 1995, 58, 131.
-
(1995)
J. Nat. Prod.
, vol.58
, pp. 131
-
-
Lounasmaa, M.1
Jokela, R.2
Hanhinen, P.3
Miettinen, J.4
Salo, J.5
-
58
-
-
0344860162
-
Socrates: "De deux maux, il faut choisir le moindre"
-
Larousse, Paris
-
Socrates: "De deux maux, il faut choisir le moindre", in "Le Petit Larousse", Grand Format 1997, Larousse, Paris, 1996, p. 1103.
-
(1996)
"Le Petit Larousse", Grand Format 1997
, pp. 1103
-
-
-
59
-
-
0344789649
-
-
note
-
13C NMR data actually point to the preponderance of a chair conformation for ring D.
-
-
-
-
60
-
-
0345220439
-
-
note
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The tentative shift values for 3a and 3b, taken from the spectrum of the tautomeric mixture of 15-epi-Z-geissoschizine (3), were mainly assigned by using the spectra of compounds (4) and (1), respectively, as models.
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