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Stereoselective Syntheses of all the Possible Stereoisomers of Coronafacic Acid

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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… Click to show full abstract

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.

Keywords: stereoisomers coronafacic; coronafacic acid; possible stereoisomers; syntheses possible; stereoselective syntheses; cfa

Journal Title: ChemistryOpen
Year Published: 2020

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