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Volumn 131, Issue 43, 2009, Pages 15909-15917

Total syntheses of (±)-platencin and (-)-platencin

Author keywords

[No Author keywords available]

Indexed keywords

ANTI-BACTERIAL ACTIVITY; ASYMMETRIC PREPARATION; BACTERIAL STRAINS; BICYCLIC KETONES; DIELS-ALDER REACTION; DIFFERENT MECHANISMS; METHICILLIN-RESISTANT STAPHYLOCOCCUS AUREUS; NATURAL PRODUCTS; ONE POT; RESISTANT STRAINS; S. AUREUS; SECONDARY METABOLITES; STREPTOMYCES PLATENSIS; TOTAL SYNTHESIS; VANCOMYCIN; VANCOMYCIN-RESISTANT ENTEROCOCCI;

EID: 70350666476     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja906801g     Document Type: Article
Times cited : (87)

References (83)
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    • For isolation of platencin, see: (a)
    • For isolation of platencin, see: (a) Wang, J.; et al. Proc. Natl. Acad. Sci. U.S.A. 2007, 104, 7612.
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    • (a) Wang, J.; et al. Nature 2006, 441, 358.
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    • For a review on the approaches to platensimycin and related analogues, see: (j)
    • For a review on the approaches to platensimycin and related analogues, see: (j) Tiefenbacher, K.; Mulzer, J. Angew. Chem., Int. Ed. 2008, 47, 2548.
    • (2008) Angew. Chem., Int. Ed. , vol.47 , pp. 2548
    • Tiefenbacher, K.1    Mulzer, J.2
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    • 51649114072 scopus 로고    scopus 로고
    • For formal syntheses of platencin, see: (c)
    • For formal syntheses of platencin, see: (c) Tiefenbacher, K.; Mulzer, J. Angew. Chem., Int. Ed. 2008, 47, 6199.
    • (2008) Angew. Chem., Int. Ed. , vol.47 , pp. 6199
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  • 58
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    • Varseev and Maier have recently described the use of an allyl enol carbonate to prepare an intermediate similar to 18 in up to 87% ee.8i
    • Varseev and Maier have recently described the use of an allyl enol carbonate to prepare an intermediate similar to 18 in up to 87% ee.8i
  • 59
    • 70350639686 scopus 로고    scopus 로고
    • Asymmetric alkylation reactions using chiral bases or chiral phase-transfer catalysts were also considered but not pursued for similar reasons
    • Asymmetric alkylation reactions using chiral bases or chiral phase-transfer catalysts were also considered but not pursued for similar reasons.
  • 67
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    • This reagent is easily prepared on a large scale using a procedure previously reported; see: (b)
    • This reagent is easily prepared on a large scale using a procedure previously reported; see: (b) Danishefsky, S.; Chackalamannil, S.; Harrison, P.; Silvestri, M. J. Am. Chem. Soc. 1985, 107, 2474.
    • (1985) J. Am. Chem. Soc. , vol.107 , pp. 2474
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  • 68
    • 70350637764 scopus 로고    scopus 로고
    • Tricyclic byproduct 21b was characterized by NMR spectroscopic analysis; structures of the corresponding byproduct, such as 21a and 21c-e, were assigned by analogy
    • Tricyclic byproduct 21b was characterized by NMR spectroscopic analysis; structures of the corresponding byproduct, such as 21a and 21c-e, were assigned by analogy.
  • 69
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    • CCDC-671740 contains the crystallographic data for compound (-)-22. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via
    • CCDC-671740 contains the crystallographic data for compound (-)-22. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.
  • 83
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    • CCDC-740150 contains the supplementary crystallographic data for compound (-)-1. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via
    • CCDC-740150 contains the supplementary crystallographic data for compound (-)-1. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.