Asymmetric Synthesis of the alpha-D-Galactosyl Ceramide KRN7000 via an Organocatalytic Aldol Reaction as Key Step

[摘要]：The asymmetric synthesis of the antitumor and immunostimulatory alpha-D-galactosyl ceramide KRN7000 using a (R)-proline-catalyzed enantioselective aldol reaction as key step is described. The title compound is synthesized in thirteen linear steps with excellent stereoselectivity (de >98%, ee = 95%) employing the commercially available substrates 1-pentadecanal, 2,2-dimethyl-1,3-dioxan-5-one, hexacosanoic acid, and D-galactose.

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