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Novel branched ether formation via conjugate reduction of an unsaturated cyanohydrin derivative and its synthetic application to the EF-ring segment of ciguatoxin

Authors
Journal
Tetrahedron Letters
0040-4039
Publisher
Elsevier
Publication Date
Volume
45
Issue
41
Identifiers
DOI: 10.1016/j.tetlet.2004.08.117
Keywords
  • Fused Medium-Ring Ether
  • Ciguatoxin
  • Branched Ether Synthesis
  • Hetero-Michael Addition

Abstract

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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