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  • 1
    Electronic Resource
    Electronic Resource
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1999 (1999), S. 751-756 
    ISSN: 1434-193X
    Keywords: Asymmetric synthesis ; Streptenol A ; Synthetic methods ; Natural products ; SAMP/RAMP hydrazones ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: -The asymmetric synthesis of (+)-streptenol A was carried out in ten steps and with high enantioselectivity (ee ≥ 96%). The key steps are the α-alkylation of 2,2-dimethyl-1,3-dioxan-5-one RAMP hydrazone A (1), subsequent deoxygenation and elaboration of the side chain via aldehyde B to furnish (+)-streptenol A in 23% overall yield. In analogy, the enantiomer (-)-streptenol A was synthesized using the corresponding SAMP hydrazone in 18% overall yield.
    Type of Medium: Electronic Resource
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  • 2
    ISSN: 1434-193X
    Keywords: Asymmetric synthesis ; Hydrazones ; Synthetic methods ; Alkylations ; Deoxygenation ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: An efficient asymmetric synthesis of protected anti-1,3-diols 5 (de ≥ 98%, ee = 92-98%) from 2,2-dimethyl-1,3-dioxan-5-one SAMP hydrazone 1 is described. The key steps are the diastereo- and enantioselective α,α′-bisalkylation followed by reduction of the ketones 2 and a variant of the Barton-McCombie deoxygenation. The new method allows the synthesis of acetonide-protected anti-1,3-diols with a broad range of substituents in good overall yields (31-69%).
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
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