-
1
-
-
0011833235
-
Monoterpenoid indole alkaloids
-
Saxton, J. E., Ed., Taylor, E. C., Ed., Wiley, New York
-
For reviews, see: (a) Sapi, J.; Massiot, G. Monoterpenoid Indole Alkaloids Saxton, J. E., Ed., In The Chemistry of Heterocyclic Compounds, Taylor, E. C., Ed., Wiley, New York, 1994, Supplement to Vol. 25, Part 4, pp. 279-355.
-
(1994)
The Chemistry of Heterocyclic Compounds
, vol.25
, Issue.PART 4
, pp. 279-355
-
-
Sapi, J.1
Massiot, G.2
-
2
-
-
1542499040
-
-
Cordell, G. A., Ed., Academic Press, New York
-
(b) Bosch, J.; Bonjoch, J.; Amat, M. In The Alkaloids, Cordell, G. A., Ed., Academic Press, New York, 1996, Vol. 48, pp 75-189.
-
(1996)
The Alkaloids
, vol.48
, pp. 75-189
-
-
Bosch, J.1
Bonjoch, J.2
Amat, M.3
-
3
-
-
0029557965
-
-
For more recent total syntheses, see: (c) Bonjoch, J.; Solé, D.; Bosch, J. J. Am. Chem. Soc. 1995, 117, 11017.
-
(1995)
J. Am. Chem. Soc.
, vol.117
, pp. 11017
-
-
Bonjoch, J.1
Solé, D.2
Bosch, J.3
-
4
-
-
0030036498
-
-
(d) Solé, D.; Bonjoch, J.; Bosch, J. J. Org. Chem. 1996, 61, 4194.
-
(1996)
J. Org. Chem.
, vol.61
, pp. 4194
-
-
Solé, D.1
Bonjoch, J.2
Bosch, J.3
-
5
-
-
0030586102
-
-
(e) Solé, D.; Bonjoch, J.; García-Rubio, S.; Suriol, R.; Bosch, J. Tetrahedron Lett. 1996, 37, 5213.
-
(1996)
Tetrahedron Lett.
, vol.37
, pp. 5213
-
-
Solé, D.1
Bonjoch, J.2
García-Rubio, S.3
Suriol, R.4
Bosch, J.5
-
6
-
-
0029818921
-
-
(f) Kuehne, M. E.; Wang, T.; Seraphin, D. J. Org. Chem. 1996, 61, 7873.
-
(1996)
J. Org. Chem.
, vol.61
, pp. 7873
-
-
Kuehne, M.E.1
Wang, T.2
Seraphin, D.3
-
7
-
-
0029909445
-
-
(g) Martin, S. F.; Clark, C. W.; Ito, M.; Mortimore, M. J. Am. Chem. Soc. 1996, 118, 9804.
-
(1996)
J. Am. Chem. Soc.
, vol.118
, pp. 9804
-
-
Martin, S.F.1
Clark, C.W.2
Ito, M.3
Mortimore, M.4
-
8
-
-
0027370231
-
-
(a) Magnus, P.; Giles, M.; Bonnert, R.; Johnson, G.; McQuire, L.; Deluca, M.; Merritt, A.; Kim, C. S.; Vicker, N. J. Am. Chem. Soc. 1993, 115, 8116.
-
(1993)
J. Am. Chem. Soc.
, vol.115
, pp. 8116
-
-
Magnus, P.1
Giles, M.2
Bonnert, R.3
Johnson, G.4
McQuire, L.5
Deluca, M.6
Merritt, A.7
Kim, C.S.8
Vicker, N.9
-
9
-
-
0029049371
-
-
(b) Amat, M.; Coll, M.-D.; Bosch, J. Tetrahedron 1995, 51, 10759.
-
(1995)
Tetrahedron
, vol.51
, pp. 10759
-
-
Amat, M.1
Coll, M.-D.2
Bosch, J.3
-
10
-
-
0028963393
-
-
Micouin, L.; Diez, A.; Castells, J.; López, D.; Rubiralta, M.; Quirion, J.-C.; Husson, H.-P. Tetrahedron Lett. 1995, 36, 1693.
-
(1995)
Tetrahedron Lett.
, vol.36
, pp. 1693
-
-
Micouin, L.1
Diez, A.2
Castells, J.3
López, D.4
Rubiralta, M.5
Quirion, J.-C.6
Husson, H.-P.7
-
11
-
-
0030272830
-
-
For a preliminary report of part of this work, see: Amat, M.; Coll, M.-D.; Passarella, D.; Bosch, J. Tetrahedron: Asymmetry 1996, 7, 2775.
-
(1996)
Tetrahedron: Asymmetry
, vol.7
, pp. 2775
-
-
Amat, M.1
Coll, M.-D.2
Passarella, D.3
Bosch, J.4
-
12
-
-
0029003845
-
-
Knight, S. D.; Overman, L. E.; Pairaudeau, G. J. Am. Chem. Soc. 1995, 117, 5776.
-
(1995)
J. Am. Chem. Soc.
, vol.117
, pp. 5776
-
-
Knight, S.D.1
Overman, L.E.2
Pairaudeau, G.3
-
13
-
-
0342567013
-
-
unpublished
-
The synthesis of (-)-tubifolidine following the methodology reported in ref le has recently been completed in our laboratory: Bonjoch, J.; Solé, D.; García-Rubio, S.; Bosch, J., unpublished.
-
-
-
Bonjoch, J.1
Solé, D.2
García-Rubio, S.3
Bosch, J.4
-
14
-
-
0013848559
-
-
The biogenetic numbering and ring labeling is used throughout this paper: Le Men, J.; Taylor, W. I. Experientia 1965, 21, 508.
-
(1965)
Experientia
, vol.21
, pp. 508
-
-
Le Men, J.1
Taylor, W.I.2
-
15
-
-
0027941124
-
-
For the use of this strategy from 2-(4-piperidylmethyl)indoles in the synthesis of Strychnos alkaloids in the racemic series, see: Gràcia, J.; Casamitjana, N.; Bonjoch, J.; Bosch, J. J. Org. Chem. 1994, 14, 3939.
-
(1994)
J. Org. Chem.
, vol.14
, pp. 3939
-
-
Gràcia, J.1
Casamitjana, N.2
Bonjoch, J.3
Bosch, J.4
-
16
-
-
84943015962
-
-
See also ref 2a
-
For related transannular cyclizations in the synthesis of Strychnos alkaloids in the racemic series, see: Harley-Mason, J. Pure Appl. Chem. 1975, 41, 167. See also ref 2a.
-
(1975)
J. Pure Appl. Chem.
, vol.41
, pp. 167
-
-
Harley-Mason1
-
18
-
-
0000746177
-
-
Trost, B. M., Ed., Pergamon Press, Oxford, Chapter 72
-
(b) Wipf, P. In Comprehensive Organic Synthesis Trost, B. M., Ed., Pergamon Press, Oxford, 1991, Vol. 5, Chapter 72.
-
(1991)
Comprehensive Organic Synthesis
, vol.5
-
-
Wipf, P.1
-
19
-
-
0018567705
-
-
Uskokovic, M. R.; Lewis, R. L.; Partridge, J. J.; Despreaux, C. W.; Pruess, D. L. J. Am. Chem. Soc. 1979, 101, 6742.
-
(1979)
J. Am. Chem. Soc.
, vol.101
, pp. 6742
-
-
Uskokovic, M.R.1
Lewis, R.L.2
Partridge, J.J.3
Despreaux, C.W.4
Pruess, D.L.5
-
20
-
-
0001150685
-
-
Smith III, A. B.; Visnick, M.; Haseltine, J. N.; Sprengeler, P. A. Tetrahedron 1986, 42, 2957.
-
(1986)
Tetrahedron
, vol.42
, pp. 2957
-
-
Smith A.B. III1
Visnick, M.2
Haseltine, J.N.3
Sprengeler, P.A.4
-
21
-
-
0026773354
-
-
For the preparation of optically pure 1-(pyridyl)ethanols by lipase-catalyzed transesterification, see: (a) Seemayer, R.; Schneider, M. P. Tetrahedron: Asymmetry 1992, 3, 827.
-
(1992)
Tetrahedron: Asymmetry
, vol.3
, pp. 827
-
-
Seemayer, R.1
Schneider, M.P.2
-
22
-
-
0028129269
-
-
(b) Orrenius, C.; Mattson, A.; Norin, T.; Öhrner, N.; Hult, K. Tetrahedron: Asymmetry 1994, 5, 1363.
-
(1994)
Tetrahedron: Asymmetry
, vol.5
, pp. 1363
-
-
Orrenius, C.1
Mattson, A.2
Norin, T.3
Öhrner, N.4
Hult, K.5
-
23
-
-
0001667275
-
-
For other reports on the preparation of enantiopure 1-(3-pyridyl)ethanols, see: (c) Imuta, M.; Ziffer, H. J. Org. Chem. 1978, 43, 3530.
-
(1978)
J. Org. Chem.
, vol.43
, pp. 3530
-
-
Imuta, M.1
Ziffer, H.2
-
24
-
-
0000231743
-
-
(d) Ziffer, H.; Kawai, K.; Kasai, M.; Imuta, M.; Froussios, C. J. Org. Chem. 1983, 48, 3017.
-
(1983)
J. Org. Chem.
, vol.48
, pp. 3017
-
-
Ziffer, H.1
Kawai, K.2
Kasai, M.3
Imuta, M.4
Froussios, C.5
-
25
-
-
37049087702
-
-
(e) Soai, K.; Niwa, S.; Kobayashi, T. J. Chem. Soc., Chem. Commun. 1987, 801.
-
(1987)
J. Chem. Soc., Chem. Commun.
, pp. 801
-
-
Soai, K.1
Niwa, S.2
Kobayashi, T.3
-
26
-
-
0000681818
-
-
(f) Brown, H. C.; Park, W. S.; Cho, B. T.; Ramachandran, P. V. J. Org. Chem. 1987, 52, 5406.
-
(1987)
J. Org. Chem.
, vol.52
, pp. 5406
-
-
Brown, H.C.1
Park, W.S.2
Cho, B.T.3
Ramachandran, P.V.4
-
27
-
-
0001525729
-
-
(g) Takeshita, M.; Terada, K.; Akutsu, N.; Yoshida, S.; Sato, T. Heterocycles 1987, 26, 3051.
-
(1987)
Heterocycles
, vol.26
, pp. 3051
-
-
Takeshita, M.1
Terada, K.2
Akutsu, N.3
Yoshida, S.4
Sato, T.5
-
28
-
-
0000747506
-
-
(h) Brown, H. C.; Srebnik, M.; Ramachandran, P. V. J. Org. Chem. 1989, 54, 1577.
-
(1989)
J. Org. Chem.
, vol.54
, pp. 1577
-
-
Brown, H.C.1
Srebnik, M.2
Ramachandran, P.V.3
-
29
-
-
0028273220
-
-
(i) Berenguer, R.; Garcia, J.; Vilarrasa, J. Tetrahedron: Asymmetry 1994, 5, 165.
-
(1994)
Tetrahedron: Asymmetry
, vol.5
, pp. 165
-
-
Berenguer, R.1
Garcia, J.2
Vilarrasa, J.3
-
30
-
-
37049082393
-
-
See also ref cited therein
-
(j) Akakabe, Y.; Takahashi, M.; Kamezawa, M.; Kikuchi, K.; Tachibana, H.; Ohtani, T.; Naoshima, Y. J. Chem. Soc., Perkin Trans. 1 1995, 1295. See also ref cited therein.
-
(1995)
J. Chem. Soc., Perkin Trans.
, vol.1
, pp. 1295
-
-
Akakabe, Y.1
Takahashi, M.2
Kamezawa, M.3
Kikuchi, K.4
Tachibana, H.5
Ohtani, T.6
Naoshima, Y.7
-
31
-
-
0342567010
-
-
For the inversion of this unreacted S alcohol to the R enantiomer, see ref 11
-
For the inversion of this unreacted S alcohol to the R enantiomer, see ref 11.
-
-
-
-
32
-
-
0013596357
-
-
For examples of the Claisen rearrangement from 3-(1-hydroxyethyl)tetrahydropyridine derivatives, see: (a) Ziegler, F. E.; Sweeny, J. G. Tetrahedron Lett. 1969, 1097.
-
(1969)
Tetrahedron Lett.
, pp. 1097
-
-
Ziegler, F.E.1
Sweeny, J.G.2
-
35
-
-
84982064763
-
-
(d) Rackur, G.; Stahl, M.; Walkowiak, M.; Winterfeldt, E. Chem. Ber. 1976, 109, 3817.
-
(1976)
Chem. Ber.
, vol.109
, pp. 3817
-
-
Rackur, G.1
Stahl, M.2
Walkowiak, M.3
Winterfeldt, E.4
-
36
-
-
0343001387
-
-
(e) Bosch, J.; Rubiralta, M.; Bolós, J. Tetrahedron, 1987, 43, 391.
-
(1987)
Tetrahedron
, vol.43
, pp. 391
-
-
Bosch, J.1
Rubiralta, M.2
Bolós, J.3
-
37
-
-
0028210891
-
-
(f) Tirkkonen, B.; Miettinen, J.; Salo, J.; Jokela, R.; Lounasmaa, M. 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
-
38
-
-
0028866948
-
-
See also ref 11
-
(g) Takayama, H.; Maeda, M.; Ohbayashi, S.; Kitajima, M.; Sakai, S.; Aimi, N. Tetrahedron Lett. 1995, 36, 9337. See also ref 11.
-
(1995)
Tetrahedron Lett.
, vol.36
, pp. 9337
-
-
Takayama, H.1
Maeda, M.2
Ohbayashi, S.3
Kitajima, M.4
Sakai, S.5
Aimi, N.6
-
39
-
-
84960070165
-
-
For a review on the elaboration of the ethylidene substituent in the synthesis of indole alkaloids, see: Bosch, J.; Bennasar, M.-L. Heterocycles 1983, 20, 2471.
-
(1983)
Heterocycles
, vol.20
, pp. 2471
-
-
Bosch, J.1
Bennasar, M.-L.2
-
40
-
-
0001840471
-
-
For a review on the Polonovski reaction, see: Grierson, D. Org. React. 1990, 39, 85.
-
(1990)
Org. React.
, vol.39
, pp. 85
-
-
Grierson, D.1
-
42
-
-
37049115301
-
-
For related cyclizations, see: (a) Besselièvre, R.; Thal, C.; Husson, H.-P.; Potier, P. J. Chem. Soc., Chem. Comm. 1975, 90.
-
(1975)
J. Chem. Soc., Chem. Comm.
, pp. 90
-
-
Besselièvre, R.1
Thal, C.2
Husson, H.-P.3
Potier, P.4
-
43
-
-
0002908631
-
-
See also ref 15b
-
(b) Chevolot, L.; Husson, A.; Kan-Fan, C.; Husson, H.-P; Potier, P. Bull. Soc. Chim. France 1976, 1222. See also ref 15b.
-
(1976)
Bull. Soc. Chim. France
, pp. 1222
-
-
Chevolot, L.1
Husson, A.2
Kan-Fan, C.3
Husson, H.-P.4
Potier, P.5
-
44
-
-
0001687864
-
-
For the stereoselective preparation and spectroscopic data of racemic 10a, see: Bonjoch, J.; Quirante, J.; Linares, A.; Bosch, J. Heterocycles 1988, 27, 2883.
-
(1988)
Heterocycles
, vol.27
, pp. 2883
-
-
Bonjoch, J.1
Quirante, J.2
Linares, A.3
Bosch, J.4
-
46
-
-
0000879577
-
-
Padwa, A., Ed., Marcel Dekker, New York
-
(b) For a review, see: Sundberg, R. J. Organic Photochemistry Padwa, A., Ed., Marcel Dekker, New York, 1983, Vol. 6, pp 121-176.
-
(1983)
Organic Photochemistry
, vol.6
, pp. 121-176
-
-
Sundberg, R.J.1
-
47
-
-
0002201862
-
-
For a review on the dealkylation of amines with acyl chlorides, see: Cooley, J. H.; Evain, E. J. Synthesis 1989, 1.
-
(1989)
Synthesis
, pp. 1
-
-
Cooley, J.H.1
Evain, E.J.2
-
50
-
-
0027729380
-
-
See also ref 2a
-
For related photoisomerizations, see: Kuehne, M. E.; Xu, F. J. Org. Chem. 1993, 58, 7490. See also ref 2a.
-
(1993)
J. Org. Chem.
, vol.58
, pp. 7490
-
-
Kuehne, M.E.1
Xu, F.2
-
53
-
-
0021039588
-
-
See also ref 21a
-
(c) Ban, Y.; Yoshida, K.; Goto, J.; Oishi, T.; Takeda, E. Tetrahedron 1983, 39, 3657. See also ref 21a.
-
(1983)
Tetrahedron
, vol.39
, pp. 3657
-
-
Ban, Y.1
Yoshida, K.2
Goto, J.3
Oishi, T.4
Takeda, E.5
-
54
-
-
0343436990
-
-
For a similar 'spontaneous' transannular oxidative cyclization in a tetracyclic stemmademine-type system, see ref 2a
-
For a similar 'spontaneous' transannular oxidative cyclization in a tetracyclic stemmademine-type system, see ref 2a.
-
-
-
-
55
-
-
84984086724
-
-
This platinum-mediated oxidative cyclization also constitutes the last step of two different syntheses of (±)-tubifoline: see ref 26b,c
-
Schumann, D.; Schmid, H. Helv. Chim. Acta 1963, 46, 1996. This platinum-mediated oxidative cyclization also constitutes the last step of two different syntheses of (±)-tubifoline: see ref 26b,c.
-
(1963)
Helv. Chim. Acta
, vol.46
, pp. 1996
-
-
Schumann, D.1
Schmid, H.2
-
56
-
-
0001439780
-
-
For the isolation and structural elucidation of this alkaloid, see: Kump, W. G.; Patel, M. B.; Rowson, J. M.; Schmid, H. Helv. Chim. Acta 1964, 47, 1497.
-
(1964)
Helv. Chim. Acta
, vol.47
, pp. 1497
-
-
Kump, W.G.1
Patel, M.B.2
Rowson, J.M.3
Schmid, H.4
-
57
-
-
0343436988
-
-
note
-
-3. Complete data have been deposited at the Cambridge Crystallographic Data Centre.
-
-
-
-
58
-
-
0342567005
-
-
For X-ray Crystallographic analysis of pentacyclic Strychnos alkaloids, see: (a) Zeches, M.; Ravao, T.; Richard, B.; Massiot, G.; Le Men-Olivier, L.; Guilhem, J.; Pascard, C. Tetrahedron Lett. 1984, 25, 659.
-
(1984)
Tetrahedron Lett.
, vol.25
, pp. 659
-
-
Zeches, M.1
Ravao, T.2
Richard, B.3
Massiot, G.4
Le Men-Olivier, L.5
Guilhem, J.6
Pascard, C.7
-
59
-
-
0342567006
-
-
(b) Hu, W.-L.; Zhu, J.-P.; Prewo, R.; Hesse, M. Phytochemistry 1989, 28, 1963.
-
(1989)
Phytochemistry
, vol.28
, pp. 1963
-
-
Hu, W.-L.1
Zhu, J.-P.2
Prewo, R.3
Hesse, M.4
-
60
-
-
0000686657
-
-
(c) For a detailed structural study of strychnine by X-ray crystallographic methods, see: Mostad, A. Acta Chem. Scand. 1985, B39, 705.
-
(1985)
Acta Chem. Scand.
, vol.B39
, pp. 705
-
-
Mostad, A.1
-
61
-
-
0000742347
-
-
Amat, M.; Linares, A.; Bosch, J. J. Org. Chem. 1990, 55, 6299.
-
(1990)
J. Org. Chem.
, vol.55
, pp. 6299
-
-
Amat, M.1
Linares, A.2
Bosch, J.3
-
62
-
-
0027309023
-
-
(a) For previous total syntheses of racemic tubifoline and tubifolidine, see ref 26b,c and 32. The synthesis of (±)-tubifolidine has also been reported in ref le and in: Bonjoch, J.; Solé, D.; Bosch, J. J. Am. Chem. Soc. 1993, 115, 2064.
-
(1993)
J. Am. Chem. Soc.
, vol.115
, pp. 2064
-
-
Bonjoch, J.1
Solé, D.2
Bosch, J.3
-
63
-
-
0009513369
-
-
(b) For previous total syntheses of (±)-19,20-dihydroakuammicine, see ref le and 32. See also: Kuehne, M. E.; Frasier, D. A.; Spitzer, T. D. J. Org. Chem. 1991, 56, 2696.
-
(1991)
J. Org. Chem.
, vol.56
, pp. 2696
-
-
Kuehne, M.E.1
Frasier, D.A.2
Spitzer, T.D.3
-
64
-
-
0027216988
-
-
The syntheses of (±)-akuammicine constitute formal total syntheses of racemic 19,20-dihydroakuammicine: (c) Angle, S. R.; Fevig, J. M.; Knight, S. D.; Marquis, Jr., R. W.; Overman, L. E. J. Am. Chem. Soc. 1993, 115, 3966.
-
(1993)
J. Am. Chem. Soc.
, vol.115
, pp. 3966
-
-
Angle, S.R.1
Fevig, J.M.2
Knight, S.D.3
Marquis R.W., Jr.4
Overman, L.E.5
-
65
-
-
0028561864
-
-
See also ref 1d
-
(d) Kuehne, M. E.; Xu, F.; Brook, C. S. J. Org. Chem. 1994, 59, 7803. See also ref 1d.
-
(1994)
J. Org. Chem.
, vol.59
, pp. 7803
-
-
Kuehne, M.E.1
Xu, F.2
Brook, C.S.3
-
67
-
-
0011913116
-
-
Weissmann, Ch.; Schmid, H.; Karrer, P. Helv. Chim. Acta 1961, 44, 1877.
-
(1961)
Helv. Chim. Acta
, vol.44
, pp. 1877
-
-
Weissmann, Ch.1
Schmid, H.2
Karrer, P.3
|