Synthesis of the EF-ring segment of ciguatoxin CTX1B based on novel regioselective reduction of unsaturated cyanohydrins and ring-closing olefin metathesis |
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Authors: | Atsushi Takemura Ken Shimawaki Hidetoshi Kawai Takanori Suzuki |
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Affiliation: | Division of Chemistry, Graduate School of Science, Hokkaido University, Sapporo 060-0810, Japan |
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Abstract: | Aiming at a convergent total synthesis of ciguatoxin CTX1B, its EF-ring segment has been synthesized. During the synthesis, a novel method for the construction of branched ethers, based on regioselective reduction of γ-alkoxy β,γ-unsaturated α-silyloxy nitriles with borontrifluoride etherate and trialkyl silane or tributyltin hydride, has been developed. Combination use of the method and ring-closing olefin metathesis successfully provided medium-sized cyclic ethers. Efficient site-selective reduction of vinyl epoxides into homoallyl alcohols has also been developed. |
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Keywords: | Ciguatoxin CTX1B Fused medium-ring ether Ring-closing olefin metathesis Branched ether synthesis Site-selective reduction |
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