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Volumn 62, Issue 20, 1997, Pages 6855-6861

Desymmetrization of benzoic acid in the context of the asymmetric Birch reduction-alkylation protocol. Asymmetric total syntheses of (-)-eburnamonine and (-)-aspidospermidine

Author keywords

[No Author keywords available]

Indexed keywords

ASPIDOSPERMIDINE; BENZOIC ACID; UNCLASSIFIED DRUG; VINBURNINE;

EID: 0030873573     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9707592     Document Type: Article
Times cited : (113)

References (41)
  • 3
    • 0000438986 scopus 로고
    • For the asymmetric synthesis of decalin and hydrindan derivatives by palladium-catalyzed cyclization of prochiral 3,3-disubstituted-1,4-cyclohexadienes derived from benzoic acid, see: (a) Sato, Y.; Sodeoka, M.; Shibasaki, M. J. Org. Chem. 1989, 54, 4738-4739. (b) Sato, Y.; Watanabe, S.; Shilbasaki, M. Tetrahedron Lett. 1992, 33, 2589-2592. Sato, Y.; Honda, T.; Shibasaki, M. Tetrahedron Lett. 1992, 33, 2593-2596. Takemoto, T.; Nishikimi, Y.; Sodeoka, M.; Shibasaki, M. Tetrahedron Lett. 1992, 33, 3527-3530. (e) Takemoto, T.; Nishikimi, Y.; Sodeoka, M.; Shibasaki, M. Tetrahedron Lett. 1992, 33, 3531-3532. (f) Sato, Y.; Mori, M.; Shibasaki, M. Tetrahedron: Asymmetry 1995, 6, 757-766.
    • (1989) J. Org. Chem. , vol.54 , pp. 4738-4739
    • Sato, Y.1    Sodeoka, M.2    Shibasaki, M.3
  • 4
    • 0026524231 scopus 로고
    • For the asymmetric synthesis of decalin and hydrindan derivatives by palladium-catalyzed cyclization of prochiral 3,3-disubstituted-1,4-cyclohexadienes derived from benzoic acid, see: (a) Sato, Y.; Sodeoka, M.; Shibasaki, M. J. Org. Chem. 1989, 54, 4738-4739. (b) Sato, Y.; Watanabe, S.; Shilbasaki, M. Tetrahedron Lett. 1992, 33, 2589-2592. Sato, Y.; Honda, T.; Shibasaki, M. Tetrahedron Lett. 1992, 33, 2593-2596. Takemoto, T.; Nishikimi, Y.; Sodeoka, M.; Shibasaki, M. Tetrahedron Lett. 1992, 33, 3527-3530. (e) Takemoto, T.; Nishikimi, Y.; Sodeoka, M.; Shibasaki, M. Tetrahedron Lett. 1992, 33, 3531-3532. (f) Sato, Y.; Mori, M.; Shibasaki, M. Tetrahedron: Asymmetry 1995, 6, 757-766.
    • (1992) Tetrahedron Lett. , vol.33 , pp. 2589-2592
    • Sato, Y.1    Watanabe, S.2    Shilbasaki, M.3
  • 5
    • 0026524232 scopus 로고
    • For the asymmetric synthesis of decalin and hydrindan derivatives by palladium-catalyzed cyclization of prochiral 3,3-disubstituted-1,4-cyclohexadienes derived from benzoic acid, see: (a) Sato, Y.; Sodeoka, M.; Shibasaki, M. J. Org. Chem. 1989, 54, 4738-4739. (b) Sato, Y.; Watanabe, S.; Shilbasaki, M. Tetrahedron Lett. 1992, 33, 2589-2592. Sato, Y.; Honda, T.; Shibasaki, M. Tetrahedron Lett. 1992, 33, 2593-2596. Takemoto, T.; Nishikimi, Y.; Sodeoka, M.; Shibasaki, M. Tetrahedron Lett. 1992, 33, 3527-3530. (e) Takemoto, T.; Nishikimi, Y.; Sodeoka, M.; Shibasaki, M. Tetrahedron Lett. 1992, 33, 3531-3532. (f) Sato, Y.; Mori, M.; Shibasaki, M. Tetrahedron: Asymmetry 1995, 6, 757-766.
    • (1992) Tetrahedron Lett. , vol.33 , pp. 2593-2596
    • Sato, Y.1    Honda, T.2    Shibasaki, M.3
  • 6
    • 0026735821 scopus 로고
    • For the asymmetric synthesis of decalin and hydrindan derivatives by palladium-catalyzed cyclization of prochiral 3,3-disubstituted-1,4-cyclohexadienes derived from benzoic acid, see: (a) Sato, Y.; Sodeoka, M.; Shibasaki, M. J. Org. Chem. 1989, 54, 4738-4739. (b) Sato, Y.; Watanabe, S.; Shilbasaki, M. Tetrahedron Lett. 1992, 33, 2589-2592. Sato, Y.; Honda, T.; Shibasaki, M. Tetrahedron Lett. 1992, 33, 2593-2596. Takemoto, T.; Nishikimi, Y.; Sodeoka, M.; Shibasaki, M. Tetrahedron Lett. 1992, 33, 3527-3530. (e) Takemoto, T.; Nishikimi, Y.; Sodeoka, M.; Shibasaki, M. Tetrahedron Lett. 1992, 33, 3531-3532. (f) Sato, Y.; Mori, M.; Shibasaki, M. Tetrahedron: Asymmetry 1995, 6, 757-766.
    • (1992) Tetrahedron Lett. , vol.33 , pp. 3527-3530
    • Takemoto, T.1    Nishikimi, Y.2    Sodeoka, M.3    Shibasaki, M.4
  • 7
    • 0026625457 scopus 로고
    • For the asymmetric synthesis of decalin and hydrindan derivatives by palladium-catalyzed cyclization of prochiral 3,3-disubstituted-1,4-cyclohexadienes derived from benzoic acid, see: (a) Sato, Y.; Sodeoka, M.; Shibasaki, M. J. Org. Chem. 1989, 54, 4738-4739. (b) Sato, Y.; Watanabe, S.; Shilbasaki, M. Tetrahedron Lett. 1992, 33, 2589-2592. Sato, Y.; Honda, T.; Shibasaki, M. Tetrahedron Lett. 1992, 33, 2593-2596. Takemoto, T.; Nishikimi, Y.; Sodeoka, M.; Shibasaki, M. Tetrahedron Lett. 1992, 33, 3527-3530. (e) Takemoto, T.; Nishikimi, Y.; Sodeoka, M.; Shibasaki, M. Tetrahedron Lett. 1992, 33, 3531-3532. (f) Sato, Y.; Mori, M.; Shibasaki, M. Tetrahedron: Asymmetry 1995, 6, 757-766.
    • (1992) Tetrahedron Lett. , vol.33 , pp. 3531-3532
    • Takemoto, T.1    Nishikimi, Y.2    Sodeoka, M.3    Shibasaki, M.4
  • 8
    • 0028899410 scopus 로고
    • For the asymmetric synthesis of decalin and hydrindan derivatives by palladium-catalyzed cyclization of prochiral 3,3-disubstituted-1,4-cyclohexadienes derived from benzoic acid, see: (a) Sato, Y.; Sodeoka, M.; Shibasaki, M. J. Org. Chem. 1989, 54, 4738-4739. (b) Sato, Y.; Watanabe, S.; Shilbasaki, M. Tetrahedron Lett. 1992, 33, 2589-2592. Sato, Y.; Honda, T.; Shibasaki, M. Tetrahedron Lett. 1992, 33, 2593-2596. Takemoto, T.; Nishikimi, Y.; Sodeoka, M.; Shibasaki, M. Tetrahedron Lett. 1992, 33, 3527-3530. (e) Takemoto, T.; Nishikimi, Y.; Sodeoka, M.; Shibasaki, M. Tetrahedron Lett. 1992, 33, 3531-3532. (f) Sato, Y.; Mori, M.; Shibasaki, M. Tetrahedron: Asymmetry 1995, 6, 757-766.
    • (1995) Tetrahedron: Asymmetry , vol.6 , pp. 757-766
    • Sato, Y.1    Mori, M.2    Shibasaki, M.3
  • 9
    • 0024449383 scopus 로고
    • For the asymmetric halolactonizations (30-42% ee) of 1,4-cyclohexadienes related to 2 but with the (S)-2,5-dimethylpyrrolidine derived amide, see: Hart, D. J.; Huang, H.-C.; Krishnamurthy, R.; Schwartz, T. J. Am. Chem. Soc. 1989, 111, 7507-7519.
    • (1989) J. Am. Chem. Soc. , vol.111 , pp. 7507-7519
    • Hart, D.J.1    Huang, H.-C.2    Krishnamurthy, R.3    Schwartz, T.4
  • 10
    • 0001908212 scopus 로고
    • Cordell, G. A., Ed.; Academic Press: New York
    • Lounasmaa, M.; Toluanen, A. In The Alkaloids; Cordell, G. A., Ed.; Academic Press: New York, 1992; Vol. 42, pp 1-116.
    • (1992) The Alkaloids , vol.42 , pp. 1-116
    • Lounasmaa, M.1    Toluanen, A.2
  • 11
    • 0028568566 scopus 로고
    • and references cited therein
    • For syntheses of eburnamonine, see: Kaufman, M. D.; Grieco, P. A. J. Org. Chem. 1994, 59, 7197-7198 and references cited therein.
    • (1994) J. Org. Chem. , vol.59 , pp. 7197-7198
    • Kaufman, M.D.1    Grieco, P.A.2
  • 12
    • 77957029008 scopus 로고
    • Manske, R H. F., Ed.; Academic Press: New York
    • Cordell, G. A. In The Alkaloids; Manske, R H. F., Ed.; Academic Press: New York, 1979; Vol. 17, pp 199-384.
    • (1979) The Alkaloids , vol.17 , pp. 199-384
    • Cordell, G.A.1
  • 13
    • 0025021186 scopus 로고
    • and references cited therein
    • For syntheses of aspidospermidine, see: Node, M.; Nagasawa, H.; Fuji, K. J. Org. Chem. 1990, 55, 517-521 and references cited therein.
    • (1990) J. Org. Chem. , vol.55 , pp. 517-521
    • Node, M.1    Nagasawa, H.2    Fuji, K.3
  • 27
    • 9844228029 scopus 로고    scopus 로고
    • note
    • 2H.
  • 30
    • 9844234383 scopus 로고    scopus 로고
    • note
    • 2OH has been reported to give a 1:1 mixture of the C(3) α- and β-epimers; see refs 7 and 22.
  • 32
    • 4243241249 scopus 로고
    • For discussions of mechanisms for cyclization and isomerization in Pictet-Spengter type condensations, see: (a) Cox, E. D.; Cook, J. M. Chem. Rev. 1995, 95, 1797-1842. (b) Cox, E. D.; Li, J.; Hamaker, L. K.; Yu, P.; Cook, J. M. J. Chem. Soc., Chem. Commun. 1996, 2477-2478.
    • (1995) Chem. Rev. , vol.95 , pp. 1797-1842
    • Cox, E.D.1    Cook, J.M.2
  • 33
    • 0010441110 scopus 로고    scopus 로고
    • For discussions of mechanisms for cyclization and isomerization in Pictet-Spengter type condensations, see: (a) Cox, E. D.; Cook, J. M. Chem. Rev. 1995, 95, 1797-1842. (b) Cox, E. D.; Li, J.; Hamaker, L. K.; Yu, P.; Cook, J. M. J. Chem. Soc., Chem. Commun. 1996, 2477-2478.
    • (1996) J. Chem. Soc., Chem. Commun. , pp. 2477-2478
    • Cox, E.D.1    Li, J.2    Hamaker, L.K.3    Yu, P.4    Cook, J.M.5
  • 35
  • 36
    • 9844264987 scopus 로고    scopus 로고
    • note
    • Under these reaction conditions, a 20% yield of the bicyclic lactam v also was obtained. It was found that v underwent decomposition during prolonged exposure to refluxing acetic acid rather than conversion to the acetate derivative of hydroxy lactam 22.


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