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For precedent ofprenyl migration from C-3 to C-2 triggered by ring opening in related systems, see: (a) Nakagawa, N. M.; Matsuki, K.; Hasumi, K.; Taniguchi, M.; Hino, T. Heterocycles 1982, 19, 156 (symposium abstract). (b) Hino, T.; Hasumi, K.; Yamaguchi, H.; Taniguchi, M.; Nakagawa, M. Chem. Pharm. Bull. 1985, 33, 5202-5206. (c) Plate, R.; Ottenheijm, H. C. J. Tetrahedron Lett. 1986, 27, 3755-3758.
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For precedent ofprenyl migration from C-3 to C-2 triggered by ring opening in related systems, see: (a) Nakagawa, N. M.; Matsuki, K.; Hasumi, K.; Taniguchi, M.; Hino, T. Heterocycles 1982, 19, 156 (symposium abstract). (b) Hino, T.; Hasumi, K.; Yamaguchi, H.; Taniguchi, M.; Nakagawa, M. Chem. Pharm. Bull. 1985, 33, 5202-5206. (c) Plate, R.; Ottenheijm, H. C. J. Tetrahedron Lett. 1986, 27, 3755-3758.
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For precedent ofprenyl migration from C-3 to C-2 triggered by ring opening in related systems, see: (a) Nakagawa, N. M.; Matsuki, K.; Hasumi, K.; Taniguchi, M.; Hino, T. Heterocycles 1982, 19, 156 (symposium abstract). (b) Hino, T.; Hasumi, K.; Yamaguchi, H.; Taniguchi, M.; Nakagawa, M. Chem. Pharm. Bull. 1985, 33, 5202-5206. (c) Plate, R.; Ottenheijm, H. C. J. Tetrahedron Lett. 1986, 27, 3755-3758.
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See also. (b) Crich, D.; Natarajan, S. J. Org. Chem. 1995, 60, 6237-6241 and references therein.
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See ref 23a, and also: (a) Sammes, P. G.; Weedon, A. C. J. Chem. Soc., Perkin Trans. 1 1979, 3048-3052. (b) Caballero, E.; Avendaño, C.; Menéndez, J. C. Tetrahedron: Asymmetry 1998, 9, 967-981. (c) Taniguchi, M.; Yamamoto, I.; Nakagawa, M.; Hino, T. Chem. Pharm. Bull. 1985, 33, 4783-4791.
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See ref 23a, and also: (a) Sammes, P. G.; Weedon, A. C. J. Chem. Soc., Perkin Trans. 1 1979, 3048-3052. (b) Caballero, E.; Avendaño, C.; Menéndez, J. C. Tetrahedron: Asymmetry 1998, 9, 967-981. (c) Taniguchi, M.; Yamamoto, I.; Nakagawa, M.; Hino, T. Chem. Pharm. Bull. 1985, 33, 4783-4791.
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46
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0042653194
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note
-
Compound 3 has been prepared from N-Cbz-L-prolyl-L-tryptophan methyl ester (ref 8). Our procedure employing the N-Boc derivative is more convenient and can be found in Supporting Information.
-
-
-
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47
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0003686469
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-
Prenyl iodide used in this experiment was prepared in 71% yield from prenyl alcohol and Olah's chlorotrimethylsilane/sodium iodide reagent. See: Olah, G. A.; Narang, S. B.; Gupta, B.; Malhotra, R. J. Org. Chem. 1979, 44, 1247-1251.
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(a) Joule, J. A.; Mills, K.; Smith, G. F. Heterocyclic Chemistry, 3rd ed.; Chapman & Hall: New York, 1995; p 303.
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Paquette, L. A., Ed.; John Wiley and Sons: New York
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For a review of the biosynthesis of prenylated alkaloids derived from tryptophan, see: Williams, R. M.; Stocking, E. M.; Sanz-Cervera, J. F. Top. Curr. Chem. 2000, 209, 98-173.
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56
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0043154109
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(d) Grundon, M. F.; Hamblin, M. R.; Harrison, D. M.; Logue, J. N. D.; Maguire, M.; McGrath, J. A. J. Chem. Soc., Perkin Trans. 1 1980, 1294-1298.
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57
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0042653190
-
-
See also ref 18
-
(e) See also ref 18.
-
-
-
-
58
-
-
0042653189
-
-
note
-
3, 63 MHz): δ 168.1; 166.0; 147.5; 135.5; 132.8; 128.4; 123.0; 119.3; 118.9; 109.4; 80.9; 60.7; 59.8; 56.2; 45.2; 38.7; 35.4; 27.8; 26.1; 23.3; 18.1.
-
-
-
-
59
-
-
0043154112
-
-
note
-
3): δ -76.00 (s).
-
-
-
-
60
-
-
0042152132
-
-
note
-
3): δ -76.1 (s).
-
-
-
-
61
-
-
0017062253
-
-
For its preparation see ref 24b
-
Compound 10 has been isolated from natural sources. See, for instance: Hamasaki, T.; Nagayama, K.; Hatsuda, Y. Agric. Biol. Chem. 1976, 40, 2487. For its preparation, see ref 24b.
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Hamasaki, T.1
Nagayama, K.2
Hatsuda, Y.3
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