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

Naoki Ushida, Nobukazu Nagai, Masaatsu Adachi, Toshio Nishikawa

Research output: Contribution to journalArticle

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.

Original languageEnglish
Pages (from-to)977-981
Number of pages5
JournalSynlett
Volume30
Issue number8
DOIs
Publication statusPublished - 2019 Jan 1
Externally publishedYes

Keywords

  • Diels-Alder reaction
  • glycolipid
  • organocatalyst
  • RCAI-56
  • α-carbagalactose

ASJC Scopus subject areas

  • Organic Chemistry

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