Convergent synthesis of the FGHI ring system of yessotoxin: stereoselective construction of the G ring |
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Authors: | Koji Watanabe |
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Affiliation: | Department of Chemistry, Graduate School of Science, Osaka University, Toyonaka, Osaka 560-0043, Japan |
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Abstract: | A convergent synthetic route to the FGHI ring system of yessotoxin, a marine ladder polyether, has been developed. The synthesis features convergent coupling of the diol and the aldehyde to form α-cyano ethers via acetal formation followed by ring closing metathesis and reductive etherification to construct the oxocane ring G and tetrahydropyran ring H, respectively. The β-methyl group on the G ring was stereoselectively introduced by alkylation of the corresponding ketone. |
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Keywords: | Yessotoxin Convergent synthesis Polyether α-Cyano ether Acetal cleavage Ring closing metathesis Alkylation Reductive etherification |
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