TY - JOUR
T1 - Synthesis of Xanthanolides including new acylations and their synthetic applications
AU - Shindo, Mitsuru
AU - Matsumoto, Kenji
PY - 2013
Y1 - 2013
N2 - Xanthanolides were synthesized with intramolecular acylation of organolithium forming a sevenmembered carbocycle and one-pot acylation-Wittig lactonization as key steps. The Cu(II) complex efficiently catalyzed the acylation of thioester in Wittig lactonization under neutral conditions. Using the Cu(II) catalyst, symmetric dithiomalonates were converted into dissymmetric S,O-malonates via selective monoacylation. The key step in this reaction was the thermal formation of an acylketene, the stability of which would contribute to selectivity.
AB - Xanthanolides were synthesized with intramolecular acylation of organolithium forming a sevenmembered carbocycle and one-pot acylation-Wittig lactonization as key steps. The Cu(II) complex efficiently catalyzed the acylation of thioester in Wittig lactonization under neutral conditions. Using the Cu(II) catalyst, symmetric dithiomalonates were converted into dissymmetric S,O-malonates via selective monoacylation. The key step in this reaction was the thermal formation of an acylketene, the stability of which would contribute to selectivity.
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U2 - 10.5059/yukigoseikyokaishi.71.1152
DO - 10.5059/yukigoseikyokaishi.71.1152
M3 - Article
AN - SCOPUS:84893959644
VL - 71
SP - 1152
EP - 1162
JO - Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry
JF - Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry
SN - 0037-9980
IS - 11
ER -