4.7 Article

Synthesis of Enantiomerically Pure (8S,9S,10R,6Z)-Trihydroxyoctadec-6-enoic Acid

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 82, Issue 10, Pages 5146-5154

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.7b00376

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Funding

  1. Ministry of Education, Culture, Sports, Science and Technology (MEXT) of Japan
  2. Special Coordination Funds for Promoting Science and Technology, Creation of Innovation Centers for Advanced Interdisciplinary Research Areas (Innovative Bioproduction Kobe), MEXT, Japan
  3. Grants-in-Aid for Scientific Research [16K18844] Funding Source: KAKEN

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We have accomplished the asymmetric synthesis of (8S,9S,10R,6Z)-trihydroxyoctadec-6-enoic acid in optically pure form and determined the absolute configuration of the natural product on the basis of the stereodetermined chiral building block 7, which was prepared by the catalytic enantioselective allylic oxidation of 4,5-epoxycyclohex-1-ene using an S-configured N,N-bidentate ligand copper catalyst.

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