ChemistryOpen (Oct 2020)

Stereoselective Syntheses of all the Possible Stereoisomers of Coronafacic Acid

  • Raku Watanabe,
  • Dr. Nobuki Kato,
  • Kengo Hayashi,
  • Sho Tozawa,
  • Dr. Yusuke Ogura,
  • Prof. Shigefumi Kuwahara,
  • Prof. Minoru Ueda

DOI
https://doi.org/10.1002/open.202000210
Journal volume & issue
Vol. 9, no. 10
pp. 1008 – 1017

Abstract

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Abstract An efficient and stereoselective syntheses of all the possible stereoisomers of coronafacic acid (CFA) has been developed. The stereochemistries of C3a and C7a were controlled in a diastereoselective Diels‐Alder type cycloaddition using a chiral auxiliary. CFA and 6‐epi‐CFA were synthesized by hydrogenation of a common intermediate. During the synthesis of 6‐epi‐CFA, we established that its cis‐fused configuration is important for the introduction of C4‐C5 double bond by dehydration. This report is the first practical synthesis of both 6‐epi‐CFA, and its enantiomer.

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