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Volumn 50, Issue 10, 2011, Pages 2297-2301

Total synthesis and absolute stereochemistry of seragakinone A

Author keywords

Antibiotics; Cyclization; Natural products; Organocatalysis; Total synthesis

Indexed keywords

ABSOLUTE STEREOCHEMISTRY; ASYMMETRIC TOTAL SYNTHESIS; CHEMICAL EQUATIONS; CYCLIZATIONS; N-HETEROCYCLIC CARBENES; NATURAL PRODUCTS; ORGANOCATALYSIS; PINACOLS; TOTAL SYNTHESIS;

EID: 79952055800     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201006528     Document Type: Article
Times cited : (61)

References (55)
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    • For preparation and cyclocondensation of nitrile oxide, see: a
    • For preparation and cyclocondensation of nitrile oxide, see: a) J. W. Bode, Y. Hachisu, T. Matsuura, K. Suzuki, Org. Lett. 2003, 5, 391-394;
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    • note
    • Because the cyclocondensation of nitrile oxide with 3-hydroxy quinone monoacetal gave the isoxazole in low yield (see Ref. [5d]) a two-step protocol of cycloaddition and subsequent dehydrogenation was devised. The scope and limitations will be reported elsewhere.
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    • note
    • For the assignment of the absolute stereochemistry see Ref. [14]. The enantiomeric excess was assessed by HPLC analysis using a chiral stationary phase; see the Supporting Information.
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    • Use of the prenylbarium reagent resulted in poor reproducibility in this instance: A. Yanagisawa
    • Use of the prenylbarium reagent resulted in poor reproducibility in this instance: A. Yanagisawa, S. Habaue, K. Yasue, H. Yamamoto, J. Am. Chem. Soc. 1994, 116, 6130-6141.
    • (1994) J. Am. Chem. Soc. , vol.116 , pp. 6130-6141
    • Habaue, S.1    Yasue, K.2    Yamamoto, H.3
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    • note
    • 2). (Chemical Equation Presented)
  • 33
    • 79952046919 scopus 로고    scopus 로고
    • note
    • 3, vapor diffusion) was subjected to X-ray analysis. The thermal ellipsoids are shown at 50% probability. DMAP = 4-dimethylaminopyridine. (Chemical Equation Presented)
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    • 79952066913 scopus 로고    scopus 로고
    • CCDC 783964 (17), 783965 (32), and 783966 (28) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from via
    • CCDC 783964 (17), 783965 (32), and 783966 (28) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data- request/cif.
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    • note
    • 2) were much less effective.
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    • Purification of 1 by preparative TLC methods using a diolmodified silica-gel plate caused tailing, which decreased the yield of isolated product. In contrast, high-speed counter-current chromatography (HSCCC) enabled us to purify 1 without any loss of the material. See the Supporting Information. For a review on HSCCC, see
    • Purification of 1 by preparative TLC methods using a diolmodified silica-gel plate caused tailing, which decreased the yield of isolated product. In contrast, high-speed counter-current chromatography (HSCCC) enabled us to purify 1 without any loss of the material. See the Supporting Information. For a review on HSCCC, see; Y. Ito, J. Chromatogr. A 2005, 1065, 145-168.
    • (2005) J. Chromatogr. A , vol.1065 , pp. 145-168
    • Ito, Y.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.