Stereoselective Syntheses of all the Possible Stereoisomers of Coronafacic Acid

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 hydro...

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Detalles Bibliográficos
Autores principales: Watanabe, Raku, Kato, Nobuki, Hayashi, Kengo, Tozawa, Sho, Ogura, Yusuke, Kuwahara, Shigefumi, Ueda, Minoru
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2020
Materias:
Full Papers
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7545439/
https://www.ncbi.nlm.nih.gov/pubmed/33072470
http://dx.doi.org/10.1002/open.202000210
Descripción
Sumario: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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