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(a) Joule, J. A. Indoles, The Monoterpenoid Indole Alkaloids; Saxton, J. E., Ed. In The Chemistry of Heterocyclic Compounds; Weissberger, A., Taylor, E. C., Eds.; Wiley: New York, 1983; Vol. 25, Part 4, pp 232-239.
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0343508469
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Kisakürek, M.V.1
Leeuwenberg, A.J.M.2
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4
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0013848559
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The biogenetic numbering is used throughout this paper for all tetracyclic compounds. Le Men, J.; Taylor, W. I. Experientia 1965, 21, 508.
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Le Men, J.1
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5
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0017379474
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Andriantsiferana, M.; Besselièvre, R.; Riche, C.; Husson, H.-P. Tetrahedron Lett. 1977, 2587.
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Andriantsiferana, M.1
Besselièvre, R.2
Riche, C.3
Husson, H.-P.4
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7
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0006981793
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Bui, A.-M.; Debray, M.-M.; Boiteau, P.; Potier, P. Phytochemistry 1977, 16, 703.
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Bui, A.-M.1
Debray, M.-M.2
Boiteau, P.3
Potier, P.4
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8
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0006911304
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Vecchietti, V.; Ferrari, G.; Orsini, F.; Pelizzoni, F.; Zajotti, A. Phytochemistry 1978, 17, 835.
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Vecchietti, V.1
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Pelizzoni, F.4
Zajotti, A.5
-
9
-
-
0028812354
-
-
The trans C/D ring junction is present in isomethuenine (16-epimethuenine), 6-oxo-16-episihcine, and 16-episilicine: Clivio, P.; Richard, B.; Nuzillard, J.-M.; Zèches-Hanrot, M. Phytochemistry 1995, 40, 987.
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Zèches-Hanrot, M.4
-
11
-
-
0008366532
-
-
The biogenetic relationship between the alkaloids of the vobasine and ervatamine groups through an intermediate like A has been demonstrated: (a) Husson, A.; Langlois Y.; Riche, C.; Husson, H.-P.; Potier, P. Tetrahedron 1973, 29, 3095. (b) Thal, C.; Dufour, M.; Potier, P.; Jaouen, M.; Mansuy, D. J. Am. Chem. Soc. 1981, 103, 4956.
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Husson, A.1
Langlois, Y.2
Riche, C.3
Husson, H.-P.4
Potier, P.5
-
12
-
-
0019443225
-
-
The biogenetic relationship between the alkaloids of the vobasine and ervatamine groups through an intermediate like A has been demonstrated: (a) Husson, A.; Langlois Y.; Riche, C.; Husson, H.-P.; Potier, P. Tetrahedron 1973, 29, 3095. (b) Thal, C.; Dufour, M.; Potier, P.; Jaouen, M.; Mansuy, D. J. Am. Chem. Soc. 1981, 103, 4956.
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Thal, C.1
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Mansuy, D.5
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13
-
-
8544224520
-
-
Ervitsine and a methuenine-type compound have been correlated in vitro: see reference 4
-
Ervitsine and a methuenine-type compound have been correlated in vitro: see reference 4.
-
-
-
-
14
-
-
0001568162
-
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Husson, H.-P.; Bannai, K.; Freire, R.; Mompon, B.; Reis, F. A. M. Tetrahedron 1978, 34, 1363.
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0000103693
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(a) Grierson, D. S.; Harris, M.; Husson, H.-P.; Tetrahedron 1983, 39, 3683.
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Grierson, D.S.1
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0342828120
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(b) Bosch, J.; Rubiralta, M.; Domingo, A.; Bolós, J.; Linares, A.; Minguillón, C.; Amat, M.; Bonjoch, J. J. Org. Chem. 1985, 50, 1516.
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(c) Bosch, J.; Rubiralta, M.; Bolos, J. Tetrahedron 1987, 43, 391.
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(e) Rubiralta, M.; Marco, M.-P.; Bolós, J.; Trapé, J. Tetrahedron 1991, 47, 5585.
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8544224519
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Husson, H.-P. In Indole and Biogenetically Related Alkaloids; Phillipson, J. D., Zenk, M. H., Eds.; Academic Press: London, 1980; Chapter 10.
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Husson, H.-P.1
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For more recent work, see: (b) Bennasar, M.-L.; Zulaica, E.; Ramírez, A.; Bosch, J. J. Org. Chem. 1996, 67, 1239.
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(c) Bennasar, M.-L.; Zulaica, E.; Sufi, B. A.; Bosch, J. Tetrahedron 1996, 52, 8601.
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(d) Bennasar, M.-L.; Jiménez, J.-M.; Sufi, B. A.; Bosch, J. Tetrahedron Lett. 1996, 37, 9105.
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28
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0019455323
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The addition of stabilized carbon nucleophiles to N-alkyl-β-acylpyridinium salts for alkaloid synthesis was first used by Wenkert: (a) Wenkert, E. Pure Appl. Chem. 1981, 53, 1271. (b) Wenkert, E.; Guo, M.; Pestchanker, M. J.; Shi, Y.-J.; Vankar, Y. D. J. Org. Chem. 1989, 54, 1166 and refs cited therein. See also: (c) Spitzner, D.; Arnold, K.; Stezowski, J. J.; Hildenbrand, T.; Henkel, S. Chem. Ber. 1989, 122, 2027. (d) Amann, R.; Arnold, K.; Spitzner, D.; Majer, Z.; Snatzke, G. Liebigs Ann. Chem. 1996, 349.
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0024513739
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and refs cited therein
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The addition of stabilized carbon nucleophiles to N-alkyl-β-acylpyridinium salts for alkaloid synthesis was first used by Wenkert: (a) Wenkert, E. Pure Appl. Chem. 1981, 53, 1271. (b) Wenkert, E.; Guo, M.; Pestchanker, M. J.; Shi, Y.-J.; Vankar, Y. D. J. Org. Chem. 1989, 54, 1166 and refs cited therein. See also: (c) Spitzner, D.; Arnold, K.; Stezowski, J. J.; Hildenbrand, T.; Henkel, S. Chem. Ber. 1989, 122, 2027. (d) Amann, R.; Arnold, K.; Spitzner, D.; Majer, Z.; Snatzke, G. Liebigs Ann. Chem. 1996, 349.
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Vankar, Y.D.5
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30
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0342639697
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The addition of stabilized carbon nucleophiles to N-alkyl-β-acylpyridinium salts for alkaloid synthesis was first used by Wenkert: (a) Wenkert, E. Pure Appl. Chem. 1981, 53, 1271. (b) Wenkert, E.; Guo, M.; Pestchanker, M. J.; Shi, Y.-J.; Vankar, Y. D. J. Org. Chem. 1989, 54, 1166 and refs cited therein. See also: (c) Spitzner, D.; Arnold, K.; Stezowski, J. J.; Hildenbrand, T.; Henkel, S. Chem. Ber. 1989, 122, 2027. (d) Amann, R.; Arnold, K.; Spitzner, D.; Majer, Z.; Snatzke, G. Liebigs Ann. Chem. 1996, 349.
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Spitzner D1
Arnold, K.2
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Hildenbrand, T.4
Henkel, S.5
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31
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33748909888
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The addition of stabilized carbon nucleophiles to N-alkyl-β-acylpyridinium salts for alkaloid synthesis was first used by Wenkert: (a) Wenkert, E. Pure Appl. Chem. 1981, 53, 1271. (b) Wenkert, E.; Guo, M.; Pestchanker, M. J.; Shi, Y.-J.; Vankar, Y. D. J. Org. Chem. 1989, 54, 1166 and refs cited therein. See also: (c) Spitzner, D.; Arnold, K.; Stezowski, J. J.; Hildenbrand, T.; Henkel, S. Chem. Ber. 1989, 122, 2027. (d) Amann, R.; Arnold, K.; Spitzner, D.; Majer, Z.; Snatzke, G. Liebigs Ann. Chem. 1996, 349.
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Amann, R.1
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Majer, Z.4
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32
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0025273229
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Bennasar, M.-L.; Alvarez, M.; Lavilla, R.; Zulaica, E.; Bosch, J. J. Org. Chem. 1990, 55, 1156.
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Bennasar, M.-L.1
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Bosch, J.5
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33
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0026636257
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For a preliminary report of this part of the work, see: Bennasar, M.-L.; Zulaica, E.; Vidal, B.; Bosch, J. Tetrahedron Lett. 1992, 33, 3895.
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Bennasar, M.-L.1
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34
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0029055040
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Bennasar, M.-L.; Vidal, B.; Bosch, J. J. Org. Chem. 1995, 60, 4280.
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Bennasar, M.-L.1
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36
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0027283926
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For a preliminary report of this part of the work, see: Bennasar, M.-L.; Vidal, B.; Bosch, J. J. Am. Chem. Soc. 1993, 115, 5340.
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Bennasar, M.-L.1
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37
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0000285698
-
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There are few examples of aminomethylation of cyclic enamines: (a) Barnett, C. J.; Copley-Merriman, C. R.; Maki, J. J. Org. Chem. 1989, 54, 4795. (b) Mitch, C. H.; Zimmerman, D. M.; Snoddy, J. D.; Reel, J. K.; Cantrell, B. E. J. Org. Chem. 1991, 56, 1660.
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Barnett, C.J.1
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Maki, J.3
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38
-
-
0025973653
-
-
There are few examples of aminomethylation of cyclic enamines: (a) Barnett, C. J.; Copley-Merriman, C. R.; Maki, J. J. Org. Chem. 1989, 54, 4795. (b) Mitch, C. H.; Zimmerman, D. M.; Snoddy, J. D.; Reel, J. K.; Cantrell, B. E. J. Org. Chem. 1991, 56, 1660.
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Mitch, C.H.1
Zimmerman, D.M.2
Snoddy, J.D.3
Reel, J.K.4
Cantrell, B.E.5
-
39
-
-
8544237246
-
-
note
-
The moderate or low yields usually associated with the nucleophilic addition - cyclization sequence leading to bridged tetracyclic indole-containing systems are due both to the reversibility of the first step and to the fact that polymerization occurs to some extent during cyclization.
-
-
-
-
40
-
-
8544268877
-
-
4-Alkylidene-1,4-dihydropyridine 14 and tetracycle 4a were formed in some runs
-
4-Alkylidene-1,4-dihydropyridine 14 and tetracycle 4a were formed in some runs.
-
-
-
-
43
-
-
0001290992
-
-
(b) Kim, J. K.; Souma, Y.; Beutow, N.; Ibbeson, C.; Caserio, M. C. J. Org. Chem. 1989, 54, 1714.
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Kim, J.K.1
Souma, Y.2
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Ibbeson, C.4
Caserio, M.C.5
-
44
-
-
8544257600
-
-
note
-
A DMTSF-promoted displacement of the C-16 methylthio group by iodide ion can account for the formation of the C-16 iodo derivative 12.
-
-
-
-
45
-
-
37049088607
-
-
For a preliminary report of this part of the work, see: Bennasar, M.-L.; Vidal, B.; Bosch, J. J. Chem. Soc., Chem. Commun. 1995, 125.
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Bennasar, M.-L.1
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49
-
-
0021177272
-
-
3, see: (a) Murakami, Y.; Watanabe, T.; Kobayashi, A.; Yokoyama, Y. Synthesis 1984, 738. (b) Watanabe, T.; Kobayashi, A.; Nishiura, M.; Takahashi, H.; Usui, T.; Kamiyama, I.; Mochizuki, N.; Noritake, K.; Yokoyama, Y.; Murakami, Y. Chem. Pharm. Bull. 1991, 39, 1152.
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Murakami, Y.1
Watanabe, T.2
Kobayashi, A.3
Yokoyama, Y.4
-
50
-
-
0025737244
-
-
3, see: (a) Murakami, Y.; Watanabe, T.; Kobayashi, A.; Yokoyama, Y. Synthesis 1984, 738. (b) Watanabe, T.; Kobayashi, A.; Nishiura, M.; Takahashi, H.; Usui, T.; Kamiyama, I.; Mochizuki, N.; Noritake, K.; Yokoyama, Y.; Murakami, Y. Chem. Pharm. Bull. 1991, 39, 1152.
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Watanabe, T.1
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Usui, T.5
Kamiyama, I.6
Mochizuki, N.7
Noritake, K.8
Yokoyama, Y.9
Murakami, Y.10
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56
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0028264817
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(b) Lavilla, R.; Gotsens, T.; Gullón, F.; Bosch, J. Tetrahedron 1994, 50, 5233.
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Lavilla, R.1
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Bosch, J.4
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57
-
-
0001340185
-
-
3CN-AcOH under the conditions reported for the reduction of the carbon - carbon double bond in vinylogous urethanes: Rosentreter, U.; Born, L.; Kurz, J. J. Org. Chem. 1986, 51, 1165.
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Rosentreter, U.1
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58
-
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0029900639
-
-
For related hydrogenations, see: Bennasar, M.-L.; Vidal, B.; Lázaro, A.; Kumar, R.; Bosch, J. Tetrahedron Lett. 1996, 37, 3541.
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Bennasar, M.-L.1
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Kumar, R.4
Bosch, J.5
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60
-
-
0003397850
-
-
For examples of alkylation of enamines with grammes, see: (a) Sundberg, R. J.; Ligon, W. V.; Lin, L.-S. J. Org. Chem. 1971, 36, 2471. (b) Sainsbury, M. Synthesis 1977, 437, and references cited therein.
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Sundberg, R.J.1
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Lin, L.-S.3
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61
-
-
85066032793
-
-
and references cited therein
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For examples of alkylation of enamines with grammes, see: (a) Sundberg, R. J.; Ligon, W. V.; Lin, L.-S. J. Org. Chem. 1971, 36, 2471. (b) Sainsbury, M. Synthesis 1977, 437, and references cited therein.
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Sainsbury, M.1
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62
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0029983798
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For a preliminary report of this part of the work, see: Bennasar, M.-L.; Vidal, B.; Bosch, J. J. Org. Chem. 1996, 61, 1916.
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Bennasar, M.-L.1
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63
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-
8544264103
-
-
note
-
2-induced cyclization from a 19-deoxo analog of 2-acylindole 33a has been reported to lead to the trans C/D ring junction: see ref 12.
-
-
-
-
64
-
-
8544223824
-
-
note
-
This relative stereochemistry is the one predicted by Cram and Felkin - Anh models for the reduction of the acetyl group of 33b.
-
-
-
-
65
-
-
8544270394
-
-
Clivio, P.; Richard, B.; Zeches, M.; Le Men-Olivier, L.; Goh, S. H.; David, B.; Sevenet, T. Photochemistry 1990, 29, 2693.
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Clivio, P.1
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Sevenet, T.7
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71
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0023945217
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Gribble, G. W.; Barden, T. C.; Johnson, D. A. Tetrahedron 1988, 44, 3195.
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Gribble, G.W.1
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Johnson, D.A.3
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