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  • 1,4-Benzodioxanes  (1)
  • Circular dichroism  (1)
  • Wiley-Blackwell  (2)
  • Springer
  • 1
    Electronic Resource
    Electronic Resource
    Regioselective Synthesis of 2-and 3-Aryl-1,4-benzodioxanes (1989)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1989 (1989), S. 1147-1151 
    Details
    ISSN: 0170-2041
    Keywords: Benzofurans ; 1,4-Benzodioxanes ; Coupling, stereocontrolled oxidative ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Regioselektive Synthese von 2-und 3-Aryl-1,4-benzodioxanenFür die Synthese natürlich vorkommender Flavano- und Neolignane eignen sich in hervorragender Weise 3-Aryl- bzw. 2-Aryl-1,4-benzodioxan-Verbindungen des Typs 4d und 5d als Ausgangsstoffe. Ihre Synthese gelang mit hoher Regioselektivität durch oxidative Kupplung von Kaffeesäure-ethylester (2h) und Coniferylalkohol (1c) mit Silber-Salz (Oxid, Carbonat) bzw. Kaliumhexacyanoferrat(III).
    Notes: 3-Aryl- and 2-aryl-1,4-benzodioxane derivatives of type 4d and 5d are excellent starting compounds for the synthesis of natural flavano- and neolignans. The syntheses of 4d and 5d were achieved with high regioselectivity by oxidative coupling of caffeic acid ethyl ester (2h) and coniferyl alcohol (1c) in the presence of a silver salt (oxide, carbonate) and potassium hexacyanoferrate(III), respectively.
    Additional Material: 2 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198919890286
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  • 2
    Electronic Resource
    Electronic Resource
    Synthesis and circular dichroism of steroids with a 1,4-benzodioxane chromophore: On the absolute configuration of (-)-silandrin (1991)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1991 (1991), S. 633-641 
    Details
    ISSN: 0170-2041
    Keywords: (-)-Salandrin ; Sterids ; 1,4-Benzodioxane ; Circular dichroism ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Starting from cholesterol the three possible stereoisomeric 1,4-benzodioxanes 24, 31, 32 and a series of analogues with 2βH,3βH configuration (25-27, 29, 30) have been synthesized. The α band of the 1,4-benzodioxane chrompohore has been unequivocally identified in the CD spectra between 325-300 nm. For its Cotton effect the same helicity rule is valid as for homochirally analogous tetralins: the P/M helicity of the heteroring leads to a positive/negative CD within the α-band. The (2′R,3′R) configuration of 6 has been established by a comparison of its CD data with those of 39 and with the help of the above-mentioned helicity rule. This allows the assignement of the (2S,2′R,3′R) configuration of (-)-silandrin (3).
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.1991199101115
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