Stereoselective synthesis of decarestrictine D from a previously inaccessible (2Z,4E)-alkadienyl alcohol precursor.
[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.
Kobayashi
Yuichi
Y
Department of Biomolecular Engineering, Tokyo Institute of Technology, Box B-52, 4259 Nagatsuta-cho, Midori-ku, Yokohama 226-8501, Japan. ykobayas@bio.titech.ac.jp
Asano
Moriteru
M
Yoshida
Shinya
S
Takeuchi
Akira
A
D000438:Alcohols / Q000737:chemistry*; D000475:Alkenes / Q000737:chemistry*; D002384:Catalysis; D007783:Lactones / Q000138:chemical synthesis*; D015394:Molecular Structure; D009532:Nickel / Q000737:chemistry*; D013237:Stereoisomerism
D000438:Alcohols; D000475:Alkenes; D007783:Lactones; C073577:decarestrictine D; D009532:Nickel