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Asymmetric Total Synthesis of Isolinearol Using Low-Valence Titanium and Evaluation of Its Inhibitory Activity
Tomoki Tsuruta1, Keisuke Nishikawa1, Yukika Yoshino1
1Department of Chemistry, Graduate School of Science, Osaka Metropolitan University, 3-3-138 Sumiyoshi-ku, Osaka 558-8585, Japan.
Abstract:
The asymmetric total synthesis of isolinearol, a seco-dolastane-type diterpenoid that inhibits byssal thread formation by mussels, has been achieved. In the synthesis, the key features include an intramolecular reductive nucleophilic addition using a low-valence titanium species and the direct installation of a ketone side chain. We evaluated their biological activities using the synthetic samples and found the novel inhibitory molecules with a simplified structure exhibit high inhibitory activities against byssus formation and low toxicities.
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