Total Synthesis of (−)‐Ophiodilactone A and (−)‐Ophiodilactone B |
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| Authors: | Takaaki Matsubara Dr Keisuke Takahashi Dr Jun Ishihara Prof?Dr Susumi Hatakeyama |
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| Affiliation: | Graduate School of Biomedical Sciences, Nagasaki University, 1‐14 Bunkyo‐machi, Nagasaki 852‐8521 (Japan) |
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| Abstract: | The first asymmetric total synthesis of (?)‐ophiodilactone A and (?)‐ophiodilactone B, isolated from the ophiuroid (Ophiocoma scolopendrina), is reported. The key features of the synthesis include the highly stereocontrolled construction of the structurally congested γ‐lactone/δ‐lactone skeleton through an asymmetric epoxidation, diastereoselective iodolactonization, and intramolecular epoxide‐opening with a carboxylic acid, and biomimetic radical cyclization of ophiodilactone A to ophiodilactone B. |
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| Keywords: | asymmetric synthesis bioinspired synthesis radical coupling total synthesis |
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