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Stereoselective Syntheses of all the Possible Stereoisomers of Coronafacic Acid |
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| Authors: | Raku Watanabe Dr. Nobuki Kato Kengo Hayashi Sho Tozawa Dr. Yusuke Ogura Prof. Shigefumi Kuwahara Prof. Minoru Ueda |
| Affiliation: | 1. Graduate School of Life Science, Tohoku University, 6–3, Aramaki-Aza-Aoba, Aoba-ku, Sendai, 980-8578 Japan;2. Graduate School of Science, Tohoku University, 6–3, Aramaki-Aza-Aoba, Aoba-ku, Sendai, 980-8578 Japan;3. Laboratory of Applied Bioorganic Chemistry, Graduate School of Agricultural Science, Tohoku University, Sendai, 980–8572 Japan |
| 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: | natural products phytochemistry coronatine |