Iterative synthesis of the ABCDEF-ring system of yessotoxin and adriatoxin |
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| Authors: | Yuji Mori Toyohisa TakaseRyoji Noyori |
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| Institution: | a Faculty of Pharmacy, Meijo University, 150 Yagotoyama, Tempaku-ku, Nagoya 468-8503, Japan
b Department of Chemistry, Graduate School of Science, Nagoya University, Chikusa-ku, Nagoya 464-8602, Japan |
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| Abstract: | A stereocontrolled linear synthesis of the ABCDEF-ring system of yessotoxin and adriatoxin, diarrhetic shellfish toxins, is described. Iterative application of a tetrahydropyran synthesis by reaction of the alkylation of a sulfonyl-stabilized oxiranyl anion followed by 6-endo cyclization of a 4,5-epoxy alcohol led to the synthesis of the trans-fused hexacyclic ether system, and the seven-membered E ring was constructed by ring expansion reaction. |
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| Keywords: | polycyclic ethers marine toxins oxiranyllithiums 6-endo cyclization |
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