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Concise Stereocontrolled Synthesis of an α-Carbagalactose Segment of RCAI-56, a Candidate Anticancer Agent

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RCAI-56 is a synthetic glycolipid exhibiting a potent antitumor activity by stimulation of natural killer T cells. Tetra-O-benzyl-α-carbagalactose, an important synthetic segment of RCAI-56, was stereoselectively synthesized from 1,4-dichloro-2-butene in… Click to show full abstract

RCAI-56 is a synthetic glycolipid exhibiting a potent antitumor activity by stimulation of natural killer T cells. Tetra-O-benzyl-α-carbagalactose, an important synthetic segment of RCAI-56, was stereoselectively synthesized from 1,4-dichloro-2-butene in nine steps, including the key step of organocatalytic asymmetric Diels–Alder reaction between acrolein and 1-benzyloxybutadiene.

Keywords: stereocontrolled synthesis; rcai; concise stereocontrolled; segment rcai; synthesis carbagalactose

Journal Title: Synlett
Year Published: 2019

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