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Volumn 59, Issue 10, 2003, Pages 1627-1638

Stereoselective total synthesis of muconin

Author keywords

Annonaceous acetogenin; Antitumor agent; Muconin; Zn(BH4)2 reduction

Indexed keywords

ANTINEOPLASTIC AGENT; KETONE; MUCONIN; UNCLASSIFIED DRUG;

EID: 0037416958     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(03)00135-2     Document Type: Article
Times cited : (33)

References (36)
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    • For reviews see: (a) Rupprecht J.K., Hui Y.-H., McLaughlin J.L. J. Nat. Prod. 53:1990;237-278 (b) Fang X.-P., Rieser M.J., Gu Z.-M., Zhao G.-X., McLaughlin J.L. Phytochem. Anal. 4:1993;27-67 (c) Gu Z.-M., Zhao G.-X., Oberlies N.H., Zeng L., McLaughlin J.L. Recent Advances in Phytochemistry. Vol. 29:1995;Plenum Press, New York. pp 249-310 (d) Koert U. Synthesis. 1995;115-132 (e) Hoppe R., Scharf H.-D. Synthesis. 1995;1447-1464 (f) Figadere B. Acc. Chem. Res. 28:1995;359-365 (g) Zafra-Polo M.C., Gonzalez M.C., Estornell E., Sahpaz S., Cortes D. Phytochemistry. 42:1996;253-271 (h) Zeng L., Ye Q., Oberlies N.H., Shi G., Gu Z.-M., He K., McLaughlin J.L. Nat. Prod. Rep. 13:1996;275-306 (i) Zafra-Polo M.C., Figadere B., Gallardo T., Tormo J.R., Cortes D. Phytochemistry. 48:1998;1087-1117 (j) Alali F.Q., Liu X.-X., McLaughlin J.L. J. Nat. Prod. 62:1999;504-540. and references cited therein.
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    • For recent total synthesis see: (a) Harcken C., Bruckner R. New J. Chem. 2001;40-54 (b) Hu T.-S., Yu Q., Wu Y.-L., Wu Y. J. Org. Chem. 66:2001;853-861 (c) Maezaki N., Kojima N., Sakamoto A., Iwata C., Tanaka T. Org. Lett. 3:2001;429-432 (d) Burke S.D., Jiang L. Org. Lett. 3:2001;1953-1955 (e) Dixon D.J., Ley S.V., Reynolds D.J. Chem. Eur. J. 8:2002;1621-1636 (f) Makabe H., Hattori Y., Tanaka A., Oritani T. Org. Lett. 4:2002;1083-1085. and references cited therein.
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  • 12
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    • For recent total synthesis see: (a) Harcken C., Bruckner R. New J. Chem. 2001;40-54 (b) Hu T.-S., Yu Q., Wu Y.-L., Wu Y. J. Org. Chem. 66:2001;853-861 (c) Maezaki N., Kojima N., Sakamoto A., Iwata C., Tanaka T. Org. Lett. 3:2001;429-432 (d) Burke S.D., Jiang L. Org. Lett. 3:2001;1953-1955 (e) Dixon D.J., Ley S.V., Reynolds D.J. Chem. Eur. J. 8:2002;1621-1636 (f) Makabe H., Hattori Y., Tanaka A., Oritani T. Org. Lett. 4:2002;1083-1085. and references cited therein.
    • (2001) J. Org. Chem. , vol.66 , pp. 853-861
    • Hu, T.-S.1    Yu, Q.2    Wu, Y.-L.3    Wu, Y.4
  • 13
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    • For recent total synthesis see: (a) Harcken C., Bruckner R. New J. Chem. 2001;40-54 (b) Hu T.-S., Yu Q., Wu Y.-L., Wu Y. J. Org. Chem. 66:2001;853-861 (c) Maezaki N., Kojima N., Sakamoto A., Iwata C., Tanaka T. Org. Lett. 3:2001;429-432 (d) Burke S.D., Jiang L. Org. Lett. 3:2001;1953-1955 (e) Dixon D.J., Ley S.V., Reynolds D.J. Chem. Eur. J. 8:2002;1621-1636 (f) Makabe H., Hattori Y., Tanaka A., Oritani T. Org. Lett. 4:2002;1083-1085. and references cited therein.
    • (2001) Org. Lett. , vol.3 , pp. 429-432
    • Maezaki, N.1    Kojima, N.2    Sakamoto, A.3    Iwata, C.4    Tanaka, T.5
  • 14
    • 0035859355 scopus 로고    scopus 로고
    • For recent total synthesis see: (a) Harcken C., Bruckner R. New J. Chem. 2001;40-54 (b) Hu T.-S., Yu Q., Wu Y.-L., Wu Y. J. Org. Chem. 66:2001;853-861 (c) Maezaki N., Kojima N., Sakamoto A., Iwata C., Tanaka T. Org. Lett. 3:2001;429-432 (d) Burke S.D., Jiang L. Org. Lett. 3:2001;1953-1955 (e) Dixon D.J., Ley S.V., Reynolds D.J. Chem. Eur. J. 8:2002;1621-1636 (f) Makabe H., Hattori Y., Tanaka A., Oritani T. Org. Lett. 4:2002;1083-1085. and references cited therein.
    • (2001) Org. Lett. , vol.3 , pp. 1953-1955
    • Burke, S.D.1    Jiang, L.2
  • 15
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    • For recent total synthesis see: (a) Harcken C., Bruckner R. New J. Chem. 2001;40-54 (b) Hu T.-S., Yu Q., Wu Y.-L., Wu Y. J. Org. Chem. 66:2001;853-861 (c) Maezaki N., Kojima N., Sakamoto A., Iwata C., Tanaka T. Org. Lett. 3:2001;429-432 (d) Burke S.D., Jiang L. Org. Lett. 3:2001;1953-1955 (e) Dixon D.J., Ley S.V., Reynolds D.J. Chem. Eur. J. 8:2002;1621-1636 (f) Makabe H., Hattori Y., Tanaka A., Oritani T. Org. Lett. 4:2002;1083-1085. and references cited therein.
    • (2002) Chem. Eur. J. , vol.8 , pp. 1621-1636
    • Dixon, D.J.1    Ley, S.V.2    Reynolds, D.J.3
  • 16
    • 0037018447 scopus 로고    scopus 로고
    • For recent total synthesis see: (a). and references cited therein
    • For recent total synthesis see: (a) Harcken C., Bruckner R. New J. Chem. 2001;40-54 (b) Hu T.-S., Yu Q., Wu Y.-L., Wu Y. J. Org. Chem. 66:2001;853-861 (c) Maezaki N., Kojima N., Sakamoto A., Iwata C., Tanaka T. Org. Lett. 3:2001;429-432 (d) Burke S.D., Jiang L. Org. Lett. 3:2001;1953-1955 (e) Dixon D.J., Ley S.V., Reynolds D.J. Chem. Eur. J. 8:2002;1621-1636 (f) Makabe H., Hattori Y., Tanaka A., Oritani T. Org. Lett. 4:2002;1083-1085. and references cited therein.
    • (2002) Org. Lett. , vol.4 , pp. 1083-1085
    • Makabe, H.1    Hattori, Y.2    Tanaka, A.3    Oritani, T.4
  • 30
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    • 15 For an alternative synthesis of the aldehyde, see:
    • 15 For an alternative synthesis of the aldehyde, see: Sinha S.C., Sinha A., Sinha S.C., Keinan E. J. Am. Chem. Soc. 119:1997;12014-12015.
    • (1997) J. Am. Chem. Soc. , vol.119 , pp. 12014-12015
    • Sinha, S.C.1    Sinha, A.2    Sinha, S.C.3    Keinan, E.4


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