Stereoselective Synthesis of Decarestrictine D from a Previously Inaccessible (2<i>Z</i>,4<i>E</i>)-Alkadienyl Alcohol Precursor

Abstract

[reaction: see text] The core structure of decarestrictine D was constructed by stereoselective oxygenation of (2Z,4E)-alkadienyl alcohol, which could be synthesized by a nickel-catalyzed coupling reaction between the corresponding cis bromide and trans borate. Efficiency in macrocyclization of the seco acid with Yamaguchi reagent was found to be protective-group-dependent, and the best yield of 40% was obtained with the seco acid with tri-MOM protective groups.