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Stereoselective synthesis of decarestrictine D from a previously inaccessible (2Z,4E)-alkadienyl alcohol precursor
Yuichi Kobayashi1, Moriteru Asano, Shinya Yoshida
1Department of Biomolecular Engineering, Tokyo Institute of Technology, Box B-52, 4259 Nagatsuta-cho, Midori-ku, Yokohama 226-8501, Japan. ykobayas@bio.titech.ac.jp
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.
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