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    An Efficient Enantioselective Total Synthesis of a Trifluoromethyl Analogue of Blastmycinolactol.
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    Abstract An enantioselective asymmetric total synthesis of (+)‐vittatalactone has been accomplished employing enzymatic desymmetrization approach to create two methyl chiral centres. Other key steps involved are Wittig reaction, Evan's asymmetric alkylation, hydroboration, TEMPO‐BAIB‐mediated selective oxidation of 1,3‐diol and lactonization mediated by p ‐toluenesulfonyl chloride. The total synthesis was achieved by a linear synthetic sequence with an overall yield of 11.8 %.
    Desymmetrization
    Wittig reaction
    Hydroboration
    Aldol reaction
    Citations (29)
    Evolution of the synthetic strategy that culminated in the first asymmetric total synthesis of the Aspidosperma alkaloid limaspermidine is described. The successful enantioselective route to (−)-limaspermidine proceeds in 10 steps and with the isolation of only six intermediates using a Pd-catalyzed enantioselective decarboxylative allylation we have recently developed. This first enantioselective synthesis of (−)-limaspermidine establishes unambiguously its absolute configuration and allows the first asymmetric formal total synthesis of the Aspidoalbine alkaloid (−)-1-acetylaspidoalbidine.
    Formal synthesis
    Citations (41)
    Mannich reaction
    Aldol reaction
    Hydrocyanation
    Citations (19)
    A late-stage resolution of the meso-3a,3a′-bispyrrolidinoindoline unit of rac-7 in a catalytic asymmetric transformation earmarks the remarkably short, ten-step, total syntheses of hodgkinsine and hodgkinsine B. The enantioselective total synthesis of hodgkinsine B establishes the relative and absolute configuration of this trispyrrolidinoindoline alkaloid.
    Absolute Configuration
    Citations (69)
    Abstract It is proposed that asymmetric syntheses be divided into enantioselective and diastereoselective syntheses. The enantioselective hydrogenations discussed in the present progress report were catalyzed by Raney nickel that had previously been treated with solutions of optically active compounds. Relationships exist between the enantioselectivity of the catalyst and the structure of the chiral compound used to modify it.
    Raney nickel
    Asymmetric hydrogenation
    Citations (144)
    This review focuses on the enantioselective synthesis of halogenated molecules having a chiral halocarbon center. In particular, this review discusses enantioselective transformations with haloalkenes and enantioselective α-substitutions of α-halo carbonyl compounds. Enantioselective halogen-transfer reactions are excluded from this review.
    Citations (36)