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Volumn 7, Issue 4, 2005, Pages 685-688

A photochemical entry to depsides: Synthesis of gustastatin

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC AGENT; BENZOIC ACID; ESTER; GUSTASTATIN; ISOCOUMARIN DERIVATIVE; UNCLASSIFIED DRUG;

EID: 14844339766     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol047507p     Document Type: Article
Times cited : (31)

References (35)
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    • For reviews, see: (a) Yet, L. Chem. Rev. 2003, 103, 4283-4306. (b) Beutler, J. A.; McKee, T. C. Curr. Med. Chem. 2003, 10, 787-796.
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    • For selected examples, see: (a) Santesson, J. Acta Chem. Scand. 1967, 21, 1162-1172. (b) Elix, J. A.; Venables, D. A.; Wedin, M. Aust. J. Chem. 1994, 47, 1335-1344. (c) Elix, J. A.; Wardlaw, J. H. Aust. J. Chem. 2000, 53, 1007-1008.
    • (1967) Acta Chem. Scand. , vol.21 , pp. 1162-1172
    • Santesson, J.1
  • 9
    • 0343033685 scopus 로고
    • For selected examples, see: (a) Santesson, J. Acta Chem. Scand. 1967, 21, 1162-1172. (b) Elix, J. A.; Venables, D. A.; Wedin, M. Aust. J. Chem. 1994, 47, 1335-1344. (c) Elix, J. A.; Wardlaw, J. H. Aust. J. Chem. 2000, 53, 1007-1008.
    • (1994) Aust. J. Chem. , vol.47 , pp. 1335-1344
    • Elix, J.A.1    Venables, D.A.2    Wedin, M.3
  • 10
    • 0034437997 scopus 로고    scopus 로고
    • For selected examples, see: (a) Santesson, J. Acta Chem. Scand. 1967, 21, 1162-1172. (b) Elix, J. A.; Venables, D. A.; Wedin, M. Aust. J. Chem. 1994, 47, 1335-1344. (c) Elix, J. A.; Wardlaw, J. H. Aust. J. Chem. 2000, 53, 1007-1008.
    • (2000) Aust. J. Chem. , vol.53 , pp. 1007-1008
    • Elix, J.A.1    Wardlaw, J.H.2
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    • 0035823817 scopus 로고    scopus 로고
    • For selected recent examples of recorcinylic macrolide synthesis, see: (a) Garbaccio, R. M.; Stachel, S. J.; Baeschlin, D. K.; Danishefsky, S. J. J. Am. Chem. Soc. 2001, 123, 10903-10908. (b) Tichkowsky, I.; Lett, R. Tetrahedron Lett. 2002, 43, 3997-4001 and 4002-4007. (c) Barluenga, S.; Lopez, P.; Moulin, E.; Winssinger, N. Angew. Chem., Int. Ed. 2004, 43, 3467-3470.
    • (2001) J. Am. Chem. Soc. , vol.123 , pp. 10903-10908
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  • 16
    • 0037182277 scopus 로고    scopus 로고
    • For selected recent examples of recorcinylic macrolide synthesis, see: (a) Garbaccio, R. M.; Stachel, S. J.; Baeschlin, D. K.; Danishefsky, S. J. J. Am. Chem. Soc. 2001, 123, 10903-10908. (b) Tichkowsky, I.; Lett, R. Tetrahedron Lett. 2002, 43, 3997-4001 and 4002-4007. (c) Barluenga, S.; Lopez, P.; Moulin, E.; Winssinger, N. Angew. Chem., Int. Ed. 2004, 43, 3467-3470.
    • (2002) Tetrahedron Lett. , vol.43 , pp. 3997-4001
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    • 4544334262 scopus 로고    scopus 로고
    • For selected recent examples of recorcinylic macrolide synthesis, see: (a) Garbaccio, R. M.; Stachel, S. J.; Baeschlin, D. K.; Danishefsky, S. J. J. Am. Chem. Soc. 2001, 123, 10903-10908. (b) Tichkowsky, I.; Lett, R. Tetrahedron Lett. 2002, 43, 3997-4001 and 4002-4007. (c) Barluenga, S.; Lopez, P.; Moulin, E.; Winssinger, N. Angew. Chem., Int. Ed. 2004, 43, 3467-3470.
    • (2004) Angew. Chem., Int. Ed. , vol.43 , pp. 3467-3470
    • Barluenga, S.1    Lopez, P.2    Moulin, E.3    Winssinger, N.4
  • 29
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    • note
    • Under these conditions, benzhydrol (34%) and diphenyl-(tetrahydrofuran-2- yl)-methanol (33%) were also isolated, resulting from photochemistry of benzophenone, the stoicheometric byproduct from the initial benzodioxinone photolysis.
  • 30
    • 84970616619 scopus 로고    scopus 로고
    • Reference 10a
    • Isocoumarin formation is a common problem associated with o-(2-oxo-alkyl)-substituted resorcinylates, requiring the use of masked ketones in synthetic sequences. For selected examples, see: (a) Reference 10a. (b) Elix, J. A.; Jayanthi, V. K. Aust. J. Chem. 1987, 40, 1851-1859. (c) Elix, J. A.; Wardlaw, J. H. Aust. J. Chem. 1997, 4799-486.
  • 31
    • 84970616619 scopus 로고    scopus 로고
    • Isocoumarin formation is a common problem associated with o-(2-oxo-alkyl)-substituted resorcinylates, requiring the use of masked ketones in synthetic sequences. For selected examples, see: (a) Reference 10a. (b) Elix, J. A.; Jayanthi, V. K. Aust. J. Chem. 1987, 40, 1851-1859. (c) Elix, J. A.; Wardlaw, J. H. Aust. J. Chem. 1997, 4799-486.
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    • Elix, J.A.1    Jayanthi, V.K.2
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    • 84970616619 scopus 로고    scopus 로고
    • Isocoumarin formation is a common problem associated with o-(2-oxo-alkyl)-substituted resorcinylates, requiring the use of masked ketones in synthetic sequences. For selected examples, see: (a) Reference 10a. (b) Elix, J. A.; Jayanthi, V. K. Aust. J. Chem. 1987, 40, 1851-1859. (c) Elix, J. A.; Wardlaw, J. H. Aust. J. Chem. 1997, 4799-486.
    • (1997) Aust. J. Chem. , pp. 4799-5486
    • Elix, J.A.1    Wardlaw, J.H.2
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    • note
    • 8 indicated that optimal yields are obtained with an excess of one of the reactants. Optimization studies have not been performed in this particular case.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.