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Volumn 68, Issue 18, 2003, Pages 6944-6951

Brief total synthesis of the cell cycle inhibitor tryprostatin B and related preparation of its alanine analogue

Author keywords

[No Author keywords available]

Indexed keywords

CELL CYCLE INHIBITOR;

EID: 0042338580     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo034703l     Document Type: Article
Times cited : (62)

References (61)
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  • 33
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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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    • Hino, T.1    Hasumi, K.2    Yamaguchi, H.3    Taniguchi, M.4    Nakagawa, M.5
  • 34
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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.
    • (1986) Tetrahedron Lett. , vol.27 , pp. 3755-3758
    • Plate, R.1    Ottenheijm, H.C.J.2
  • 37
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    • Brossi, A., Ed.
    • (a) For a review of the chemistry of cyclic tautomers of tryptophan and tryptamines, see: Hino, T.; Nakagawa, M. In The Alkaloids; Brossi, A., Ed.; 1988; Vol. 34, pp 1-75.
    • (1988) The Alkaloids , vol.34 , pp. 1-75
    • Hino, T.1    Nakagawa, M.2
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    • and references therein
    • 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.
    • (1998) Tetrahedron: Asymmetry , vol.9 , pp. 967-981
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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.
    • (1985) Chem. Pharm. Bull. , vol.33 , pp. 4783-4791
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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.
  • 47
    • 0003686469 scopus 로고
    • 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.
    • (1979) J. Org. Chem. , vol.44 , pp. 1247-1251
    • Olah, G.A.1    Narang, S.B.2    Gupta, B.3    Malhotra, R.4
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    • See also ref 18
    • (e) See also ref 18.
  • 58
    • 0042653189 scopus 로고    scopus 로고
    • 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 scopus 로고    scopus 로고
    • note
    • 3): δ -76.00 (s).
  • 60
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    • note
    • 3): δ -76.1 (s).
  • 61
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    • 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.
    • (1976) Agric. Biol. Chem. , vol.40 , pp. 2487
    • Hamasaki, T.1    Nagayama, K.2    Hatsuda, Y.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.