Total Synthesis and Stereochemical Revision of Iriomoteolide‐2a |
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| Authors: | Keita Sakamoto Akihiro Hakamata Prof?Dr Masashi Tsuda Prof?Dr Haruhiko Fuwa |
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| Institution: | 1. Department of Applied Chemistry, Faculty of Science and Engineering, Chuo University, 1-13-27 Kasuga, Tokyo, Japan;2. Graduate School of Life Sciences, Tohoku University, Aoba-ku, Sendai, Japan;3. Center for Advanced Marine Core Research and Department of Agriculture and Marine Science, Kochi University, Nankoku, Kochi, Japan |
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| Abstract: | Total syntheses of the proposed and correct structures of iriomoteolide‐2a, a cytotoxic marine macrolide natural product with an unusual 23‐membered macrolactone skeleton, have been accomplished for the first time. The synthesis of the correct structure involves an asymmetric epoxidation/diepoxide cyclization cascade for the construction of the bis(tetrahydrofuran) moiety, a Suzuki–Miyaura coupling for the fragment assembly, and a ring‐closing metathesis for the closure of the macrocyclic backbone. In addition, the original stereochemical assignment of iriomoteolide‐2a was revised. |
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| Keywords: | cascade reactions macrocycles natural products structure elucidation total synthesis |
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