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Volumn 74, Issue 5, 2009, Pages 2046-2052

Synthetic studies on (-)-lemonomycin: An efficient asymmetric synthesis of lemonomycinone amide

Author keywords

[No Author keywords available]

Indexed keywords

ASYMMETRIC SYNTHESIS; CATALYZED CONVERSIONS; CHEMOSELECTIVE HYDROLYSIS; CONTROLLED CONDITIONS; DEBENZYLATION; DIASTEREOMER; ENANTIOSELECTIVE ALKYLATIONS; MANNICH REACTIONS; PHASE TRANSFER CATALYSTS; PICTET-SPENGLER REACTIONS; SECONDARY AMINES; STARTING MATERIALS; SYNTHETIC STUDIES; TERT-BUTYL ESTERS; TETRACYCLE; TETRAFLUOROBORATE; TETRAHYDROISOQUINOLINE; THIOETHER; TRIFLATE;

EID: 64249142616     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo8027449     Document Type: Article
Times cited : (41)

References (44)
  • 1
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    • For a comprehensive review of the chemistry and biology related to the antitumor antibiotic tetrahydroisoquinoline alkaloids, see: Scott, J. D, Williams, R. M. Chem. Rev. 2002, 102, 1669-1730
    • For a comprehensive review of the chemistry and biology related to the antitumor antibiotic tetrahydroisoquinoline alkaloids, see: Scott, J. D.; Williams, R. M. Chem. Rev. 2002, 102, 1669-1730.
  • 2
    • 56549110286 scopus 로고    scopus 로고
    • For a recent review on the syntheses of naphthyridinomycin and lemonomycin, see
    • For a recent review on the syntheses of naphthyridinomycin and lemonomycin, see: Siengalewicz, P.; Rinner, U.; Mulzer, J. Chem. Soc. Rev. 2008, 37, 2676-2690.
    • (2008) Chem. Soc. Rev , vol.37 , pp. 2676-2690
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  • 16
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    • For recent reviews, see: a, Trost, B, Fleming, I, Heathcock, C. H, Eds, Pergmon: Oxford
    • For recent reviews, see: (a) Hiemstra, H.; Speckamp, W. N. In Comprehensive Organis Synthesis; Trost, B., Fleming, I., Heathcock, C. H., Eds.; Pergmon: Oxford, 1991; Vol. 2, pp 1047-1082.
    • (1991) Comprehensive Organis Synthesis , vol.2 , pp. 1047-1082
    • Hiemstra, H.1    Speckamp, W.N.2
  • 19
    • 28844434893 scopus 로고    scopus 로고
    • Cedric Couturier, PhD thesis, Ecole Polytechnique, 17 October 2005. Cyclization using allylsilane as internal nucleophile wherein an amide group in 5 was replaced by aminonitrile function has been successfully applied to the synthesis of advanced lemonomycin intermediate and quinocarcin; see ref 9 and Kwon, S, Myers, A. G. J. Am. Chem. Soc. 2005, 127, 16796-16797
    • Cedric Couturier, PhD thesis, Ecole Polytechnique, 17 October 2005. Cyclization using allylsilane as internal nucleophile wherein an amide group in 5 was replaced by aminonitrile function has been successfully applied to the synthesis of advanced lemonomycin intermediate and quinocarcin; see ref 9 and Kwon, S.; Myers, A. G. J. Am. Chem. Soc. 2005, 127, 16796-16797.
  • 21
    • 0000860321 scopus 로고    scopus 로고
    • For intermolecular reaction of enolsilane and N-acyliminium, see: Shono, T.; Matsumura, Y.; Tsubata, K. J. Am. Chem. Soc. 1981, 103, 1172-1176.
    • For intermolecular reaction of enolsilane and N-acyliminium, see: Shono, T.; Matsumura, Y.; Tsubata, K. J. Am. Chem. Soc. 1981, 103, 1172-1176.
  • 23
    • 0034704280 scopus 로고    scopus 로고
    • For an example using amino thioether as a precursor of N-acyliminium, see: Padwa, A.; Waterson, A. G. Tetrahedron 2000, 56, 10159-10173.
    • For an example using amino thioether as a precursor of N-acyliminium, see: Padwa, A.; Waterson, A. G. Tetrahedron 2000, 56, 10159-10173.
  • 33
    • 37049109471 scopus 로고    scopus 로고
    • For 1,3-cis selective Pictet-Spengler reactions, see: (a) Massiot, G.; Mulamba, T. J. Chem. Soc., Chem. Commun. 1983, 1147-1149.
    • For 1,3-cis selective Pictet-Spengler reactions, see: (a) Massiot, G.; Mulamba, T. J. Chem. Soc., Chem. Commun. 1983, 1147-1149.
  • 42
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    • For total synthesis of bioxalomycin, see: a
    • For total synthesis of bioxalomycin, see: (a) Evans, D. A.; Illig, C. R.; Saddler, J. C. J. Am. Chem. Soc. 1986, 108, 2478-2479.
    • (1986) J. Am. Chem. Soc , vol.108 , pp. 2478-2479
    • Evans, D.A.1    Illig, C.R.2    Saddler, J.C.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.