TY - JOUR
T1 - Total Synthesis of (±)-Liphagal via Organic-Redox-Driven Palladium-Catalyzed Hydroxybenzofuran Formation
AU - Tao, Eriko
AU - Inoue, Masaki
AU - Jeong, Taejoo
AU - Kim, In Su
AU - Yoshimitsu, Takehiko
N1 - Funding Information:
The authors acknowledge Prof. Toshikatsu Takanami, Tamami Koseki, and Dr. Satoshi Hayashi at Meiji Pharmaceutical University (MPU) for their mass spectroscopic analysis. This work was supported by JSPS KAKENHI (grant number JP18K06578) (to T.Y.).
Publisher Copyright:
© 2020 American Chemical Society.
PY - 2020/7/17
Y1 - 2020/7/17
N2 - A synthetic route to liphagal, a natural PI3Kα inhibitor isolated from Aka coralliphaga, was established. The present route features an organic redox process where an alkynylquinone undergoes reductive cyclization in the presence of a hydroquinone derivative such as hydroxyquinol (1,2,4-benzenetriol) and catalytic PdCl2 to provide a substituted benzofuran suitable for accessing the natural product. The benzofuran formation takes place via the redox transformation between the alkynylquinone and the electron-rich hydroquinones followed by the concomitant Pd(II)-catalyzed oxycyclization of the resultant alkynylhydroquinone.
AB - A synthetic route to liphagal, a natural PI3Kα inhibitor isolated from Aka coralliphaga, was established. The present route features an organic redox process where an alkynylquinone undergoes reductive cyclization in the presence of a hydroquinone derivative such as hydroxyquinol (1,2,4-benzenetriol) and catalytic PdCl2 to provide a substituted benzofuran suitable for accessing the natural product. The benzofuran formation takes place via the redox transformation between the alkynylquinone and the electron-rich hydroquinones followed by the concomitant Pd(II)-catalyzed oxycyclization of the resultant alkynylhydroquinone.
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U2 - 10.1021/acs.joc.0c00965
DO - 10.1021/acs.joc.0c00965
M3 - Article
AN - SCOPUS:85087671641
VL - 85
SP - 9064
EP - 9070
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
SN - 0022-3263
IS - 14
ER -