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Total synthesis of (±)-simonsol C using dearomatization as key reaction under acidic conditions

Xiao-Yang Bi, Xiao-Shuai Yang, Shan-Shan Chen, Jia-Jun Sui, Zhao-Nan Cai, Yong-Ming Chuan and Hong-Bo Qin

Beilstein J. Org. Chem. 2025, 21, 601–606. https://doi.org/10.3762/bjoc.21.47

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Total synthesis of (±)-simonsol C using dearomatization as key reaction under acidic conditions

Xiao-Yang Bi, Xiao-Shuai Yang, Shan-Shan Chen, Jia-Jun Sui, Zhao-Nan Cai, Yong-Ming Chuan and Hong-Bo Qin

Beilstein J. Org. Chem. 2025, 21, 601–606. https://doi.org/10.3762/bjoc.21.47

How to Cite

Bi, X.-Y.; Yang, X.-S.; Chen, S.-S.; Sui, J.-J.; Cai, Z.-N.; Chuan, Y.-M.; Qin, H.-B. Beilstein J. Org. Chem. 2025, 21, 601–606. doi:10.3762/bjoc.21.47

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TY  - JOUR
A1  - Bi, Xiao-Yang
A1  - Yang, Xiao-Shuai
A1  - Chen, Shan-Shan
A1  - Sui, Jia-Jun
A1  - Cai, Zhao-Nan
A1  - Chuan, Yong-Ming
A1  - Qin, Hong-Bo
T1  - Total synthesis of (±)-simonsol C using dearomatization as key reaction under acidic conditions
JF  - Beilstein Journal of Organic Chemistry
PY  - 2025///
VL  - 21
SP  - 601
EP  - 606
SN  - 1860-5397
DO  - 10.3762/bjoc.21.47
PB  - Beilstein-Institut
JA  - Beilstein J. Org. Chem.
UR  - https://doi.org/10.3762/bjoc.21.47
KW  - acidic dearomazation
KW  - benzofuran
KW  - (±)-simonsol C
KW  - total synthesis
N2  - The total synthesis of (±)-simonsol C was accomplished using a dearomatization under acidic conditions as key step to construct an aryl-containing quaternary center. The 6/5/6 benzofuran unit was formed through reductive elimination with Zn/AcOH and a spontaneous oxy-Michael addition. This synthesis consists of 8 steps and achieves an overall yield of 13%, making it the shortest known route.
ER  -

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aromatic	the word “aromatic”
aromatic aldehyde	the word “aromatic” OR “aldehyde”
+aromatic +aldehyde	both words “aromatic” AND “aldehyde”
+aromatic -aldehyde	the word “aromatic” but NOT “aldehyde”
“aromatic aldehyde”	the exact phrase “aromatic aldehyde”
benz*	words which begin with “benz”, such as “benzene” or “benzyl”
benz*yl	words that begin with “benz” and end with “yl”, such as “benzyl” or “benzoyl”
benzyl~	words that are close to the word “benzyl”, such as “benzoyl” (i.e., fuzzy search)