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Synthesis of solamin type mono-THF acetogenins using cross-metathesis |
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| Authors: | Hiroyuki Konno Hidefumi Makabe Kazuto Nosaka |
| Institution: | a Department of Biochemical Engineering, Graduate School of Science and Technology, Yamagata University, Yonezawa, Yamagata 992-8510, Japan b Sciences of Functional Foods, Graduate School of Agriculture, Shinshu University, Minamiminowa, Kamiina, Nagano 399-4598, Japan c Department of Medicinal Chemistry, Graduate School of Medical Science, Kyoto Prefectural University of Medicine, Kita-ku, Kyoto 603-8334, Japan |
| Abstract: | The total synthesis of mono-THF acetogenins, cis-solamin A and B, and reticulatacin, was accomplished starting with muricatacin. The backbone of the mono-THF acetogenins was constructed by olefin cross-metathesis between the tetrahydrofuran moiety and γ-lactone moiety. An enzymatic kinetic transesterification procedure was successfully applied to the synthesis of an optically pure γ-lactone moiety. Notably, cis-THF compounds were obtained without using protective groups. |
| Keywords: | Annonaceous acetogenins Cross-metathesis Enzymatic transesterification Solamin Mitochondrial complex I inhibitor |
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