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Volumn 76, Issue 2, 2011, Pages 601-608

Evidence for a trianion intermediate in the metalation of 4-hydroxy-6,7-dimethoxy-8-methyl-2-naphthoic acid. methodology and application to racemic 5,5′-didesisopropyl-5,5′-dialkylapogossypol derivatives

Author keywords

[No Author keywords available]

Indexed keywords

ANTIAPOPTOTIC; BCL-2 FAMILY PROTEINS; EFFICIENT CONSTRUCTION; METALATIONS; NAPHTHOIC ACIDS; REGIO-SELECTIVE;

EID: 78651501577     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo102147s     Document Type: Article
Times cited : (8)

References (46)
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    • Ascenta Therapeutics Web site. (accessed October 27)
    • Ascenta Therapeutics Web site. http://www.ascenta.com/development/index. php#at101 (accessed October 27, 2010).
    • (2010)
  • 6
    • 78651511464 scopus 로고    scopus 로고
    • See also:; US2003008924A1
    • See also: Wang, S.; Yang, D. US2003008924A1, 2003.
    • (2003)
    • Wang, S.1    Yang, D.2
  • 19
    • 77952403302 scopus 로고    scopus 로고
    • Substitution of the methoxy group in unprotected 2-methoxy-1-naphthoic acid and 1-methoxy-2-naphthoic acid to afford the corresponding anthranilic acids occurs upon reaction with lithioamides
    • Substitution of the methoxy group in unprotected 2-methoxy-1-naphthoic acid and 1-methoxy-2-naphthoic acid to afford the corresponding anthranilic acids occurs upon reaction with lithioamides: Belaud-Rotureau, M.; Le, T. T.; Phan, T. H. T.; Nguyen, T. H.; Aissaoui, R.; Gohier, F.; Derdour, A.; Nourry, A.; Castanet, A.-S.; Nguyen, K. P. P.; Mortier, J. Org. Lett. 2010, 12, 2406-2409
    • (2010) Org. Lett. , vol.12 , pp. 2406-2409
    • Belaud-Rotureau, M.1    Le, T.T.2    Phan, T.H.T.3    Nguyen, T.H.4    Aissaoui, R.5    Gohier, F.6    Derdour, A.7    Nourry, A.8    Castanet, A.-S.9    Nguyen, K.P.P.10    Mortier, J.11
  • 21
    • 53149085620 scopus 로고    scopus 로고
    • Prepared by metalation of veratric acid with LTMP (4 equiv) at 0 °C followed by quench with iodomethane. See
    • Prepared by metalation of veratric acid with LTMP (4 equiv) at 0 °C followed by quench with iodomethane. See: Chau, N. T. T.; Nguyen, T. H.; Castanet, A.-S.; Nguyen, K. P. P.; Mortier, J. Tetrahedron 2008, 64, 10552-10557
    • (2008) Tetrahedron , vol.64 , pp. 10552-10557
    • Chau, N.T.T.1    Nguyen, T.H.2    Castanet, A.-S.3    Nguyen, K.P.P.4    Mortier, J.5
  • 29
    • 13844315856 scopus 로고    scopus 로고
    • Remetalation of 5d presumably occurs faster than destruction of the excess of LTMP by the electrophile. See
    • Remetalation of 5d presumably occurs faster than destruction of the excess of LTMP by the electrophile. See: Gohier, F.; Castanet, A.-S.; Mortier, J. J. Org. Chem. 2005, 70, 1501-1504
    • (2005) J. Org. Chem. , vol.70 , pp. 1501-1504
    • Gohier, F.1    Castanet, A.-S.2    Mortier, J.3
  • 32
    • 0037593065 scopus 로고
    • Only one example of lateral lithiation of a naphthoic acid derivative was mentioned in the literature:;, Compound A, upon treatment with LDA, was converted to a dilithium anion B which was carboxylated and hydrolyzed to give naphthaleneacetic acid C. The benzylic anion is stabilized by coordination of the lithium with the carboxylate
    • Only one example of lateral lithiation of a naphthoic acid derivative was mentioned in the literature: Hauser, F. M.; Rhee, R. J. Am. Chem. Soc. 1977, 99, 4533-4534 Compound A, upon treatment with LDA, was converted to a dilithium anion B which was carboxylated and hydrolyzed to give naphthaleneacetic acid C. The benzylic anion is stabilized by coordination of the lithium with the carboxylate.
    • (1977) J. Am. Chem. Soc. , vol.99 , pp. 4533-4534
    • Hauser, F.M.1    Rhee, R.2
  • 33
    • 2942620585 scopus 로고    scopus 로고
    • Lateral lithiations involving trianions are very scarce. See
    • Lateral lithiations involving trianions are very scarce. See: Tahara, N.; Fukuda, T.; Iwao, M. Tetrahedron Lett. 2004, 45, 5117-5120
    • (2004) Tetrahedron Lett. , vol.45 , pp. 5117-5120
    • Tahara, N.1    Fukuda, T.2    Iwao, M.3
  • 40
    • 78651502551 scopus 로고    scopus 로고
    • The protons H4,H4′ (7.60 ppm) show clear interactions with the methyl group at 2.54 ppm. There are also spatial interactions between H8,H8′ (7.50 ppm) and MeO (3.91 ppm)
    • The protons H4,H4′ (7.60 ppm) show clear interactions with the methyl group at 2.54 ppm. There are also spatial interactions between H8,H8′ (7.50 ppm) and MeO (3.91 ppm).
  • 43
    • 84855633541 scopus 로고    scopus 로고
    • Prepared from 3,4-dimethoxy-2-methylbenzoic acid (10) according to ref 14. Compound 10 was prepared by metalation of veratric acid with LTMP (4 equiv) at 0 °C followed by quench with iodomethane: see ref 13
    • Prepared from 3,4-dimethoxy-2-methylbenzoic acid (10) according to ref 14. Compound 10 was prepared by metalation of veratric acid with LTMP (4 equiv) at 0 °C followed by quench with iodomethane: see ref 13.


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