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  • 1
    Electronic Resource
    Electronic Resource
    3,4-bis(O-tert-butyldimethylsilyl)-6-O-tosyl-D-glucal: A probe for the mechanism of the iodine(III)-promoted allylic oxidation of glycals (1995)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1995 (1995), S. 2053-2056 
    Details
    ISSN: 0947-3440
    Keywords: 2,3-Anhydropyranose ; Glycal ; Hypervalent iodine ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The reaction of 3,4-bis(O-tert-butyldimethylsilyl)-6-O-tosyl-D-glucal 4 with the Koser reagent [PhI(OH)OTs] unexpectedly afforded tetrahydrofurfural 6 as well as 2,3-anhydropyranose 7 as major products. This unprecedented, stereoselective transformation helps to gain further insight into the mechanism of the well-documented hypervalent iodine-promoted allylic oxidation of cyclic enol ethers. A novel chemoenzymatic method for the preparation of glucal 4 in high yield is presented.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.1995199511289
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  • 2
    Electronic Resource
    Electronic Resource
    Synthese von rac-Norartemeseol (1991)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1991 (1991), S. 933-936 
    Details
    ISSN: 0170-2041
    Keywords: Norartemeseol, rac- ; Allyl anion, hetero-substituted ; Oxiranes, ring-opening ; Tetrahydrofuran, substituted ; Cyclopropane, vinyl- ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Synthesis of rac-NorartemeseolThe synthesis of the terpenoid rac-norartemesol (1b) is accomplished using epoxide ring-opening reactions as key steps. Thus, addition of the thio-substituted allyl anion 2b to ethylene oxide followed by proton-induced cyclisation provides the tetrahydrofuran 4a. The oxirane 6, which is formed by simple functional group interconversion, is opened by the diethylaluminium salt 10 of a propargylsilane. After catalytic hydrogenation and tosylation, fluoride-induced cyclisation of the allylsilane 13 gives the target molecule 1b.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.1991199101159
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    Paper (German National Licenses)
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