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  • Title: Enantioselective total synthesis of (+)-neosymbioimine.
    Author: Varseev GN, Maier ME.
    Journal: Org Lett; 2007 Apr 12; 9(8):1461-4. PubMed ID: 17378570.
    Abstract:
    [reaction: see text] The enantioselective total synthesis of (+)-neosymbioimine was accomplished in 18 steps from (-)-(S)-citronellol utilizing an organocatalytic alpha-oxidation of aldehyde 6. The carbon core was constructed by a tandem Horner-Wadsworth-Emmons (HWE) reaction and an intramolecular Diels-Alder cyclization. All double bonds of 12 were made in a stereoselective manner by Wittig-type reactions. Selective formation of the monosulfate monoester was accomplished by one-pot excessive sulfation followed by kinetic hydrolysis of bissulfate 18 in 79% yield.
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