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Volume 82, Issue 1
Received, 19th June, 2010, Accepted, 26th July, 2010, Published online, 27th July, 2010. |
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| Stereoselective Synthesis of Caribbean Ciguatoxin M-Ring Using [2+2] Photocyclization |
Shuji Yamashita,* Naoya Iijima, Takahiro Shida, and Masahiro Hirama*
Department of Chemistry, Graduate School of Science, Tohoku University, Aramaki, Aoba-ku, Sendai 980-8578, Japan |
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Abstract
Ciguatoxins, the principal causative toxins of ciguatera seafood poisoning, are potent toxic polycyclic ethers. We report herein a stereoselective synthesis of the seven-membered M-ring moiety of Caribbean ciguatoxin C-CTX-1. The key features of the synthesis are the photo-induced [2+2] electrocyclization and enzymatic asymmetric hydrolysis to construct the congested oxepane ring. |
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Graphical Abstract
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| Corresponding author; email: s-yamashita@m.tohoku.ac.jp |
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