Total synthesis of optically active lycopladine A by utilizing diastereoselective protection of carbonyl group in a 1,3-cyclohexanedione derivative |
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Authors: | Hiroya Kou Suwa Yoshihiro Ichihashi Yusuke Inamoto Kiyofumi Doi Takayuki |
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Affiliation: | Graduate School of Pharmaceutical Sciences, Tohoku University, Aoba-ku, Sendai, Japan. hiroya@mail.pharm.tohoku.ac.jp |
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Abstract: | We successfully synthesized two enantiomers of bicyclic enones, (7R,7aR)- and (7S,7aS)-9, from the hemiacetal 2a, which we first synthesized from the symmetrical diketone 1a via diastereoselective carbon-oxygen bond formation between one of the carbonyl groups and the chiral alcohol on the C2 side chain in a 2,2-disubstituted 1,3-cycloalkanedione derivative. We also report the total synthesis of natural (+)-lycopladine A [(+)-6] from (7R,7aR)-9 and the formal synthesis of unnatural (-)-lycopladine A [(-)-6] from (7S,7aS)-9. |
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