First Total Synthesis of (±)-6′-Methoxyretrojusticidin B Using Regiocontrolled Benzannulation: Structural Inconsistency with Procumphthalide A and Its Revision to 5′-Methoxyretrochinensin

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  • First Total Synthesis of (+/-)-6 '-Methoxyretrojusticidin B Using Regiocontrolled Benzannulation: Structural Inconsistency with Procumphthalide A and Its Revision to 5 '-Methoxyretrochinensin

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説明

We achieved the first total synthesis of a novel (+/-)-6'-methoxyretrojusticidin B, which was proposed as procumphthalide A, utilizing regiocontrolled benzannulation of an aryl(aryl')-2,2-dichlorocyclopropylmethanol as the key step. (1)H NMR spectral data suggested that the structure of the synthesized product, 6'-methoxyretrojusticidin B, was inconsistent with that of natural procumphthalide A. A computational study of the rotational barrier rationally supports the existence of a rigid chiral axis in 6'-methoxyretrojusticidin B. The revised structural elucidation of natural procumphthalide A was concluded to be 5'-methoxyretrochinensin.

収録刊行物

  • SYNLETT

    SYNLETT 2010 (15), 2275-2278, 2010-09

    GEORG THIEME VERLAG KG

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