Novel branched ether formation via conjugate reduction of an unsaturated cyanohydrin derivative and its synthetic application to the EF-ring segment of ciguatoxin |
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Authors: | Atsushi Takemura Akio Murai Hidetoshi Kawai Takanori Suzuki |
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Institution: | Division of Chemistry, Graduate School of Science, Hokkaido University, Sapporo 060-0810, Japan |
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Abstract: | A synthetic method for a branched ether system was developed. The method was based on Lewis-acid-promoted γ-position selective reduction of a γ-alkoxy β,γ-unsaturated α-silyloxy nitrile, prepared through a process including intermolecular hetero-Michael reaction of a 2-butynoate ester derivative with an alcohol. The method was efficiently applied to the synthesis of fused medium-ring ethers involving the EF-ring segment (2) of ciguatoxin (1). |
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Keywords: | Fused medium-ring ether Ciguatoxin Branched ether synthesis Hetero-Michael addition |
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