TY - JOUR
T1 - Total Synthesis of the Neuroprotective Agent Cudraisoflavone J
AU - Lu, Qili
AU - Harmalkar, Dipesh S.
AU - Quan, Guofeng
AU - Kwon, Haeun
AU - Cho, Jungsook
AU - Choi, Yongseok
AU - Lee, Dongho
AU - Lee, Kyeong
N1 - Funding Information:
This study was supported by grants from the National Research Foundation of Korea (NRF) and a grant funded by the Korea government (MSIT, NRF 2018R1A5A2023127).
Publisher Copyright:
© 2021 American Chemical Society and American Society of Pharmacognosy
PY - 2021/4/23
Y1 - 2021/4/23
N2 - Cudraisoflavone J (1), isolated fromCudrania tricuspidata, is a potent neuroprotective compound with a chiral center. Herein, we report the first total synthesis of racemic cudraisoflavone J (1) using a Claisen rearrangement and a Suzuki coupling reaction as the key steps. Racemic secondary alcohol was kinetically resolved to give (+)- and (−)-cudraisoflavone J with up to 97 and 88% enantiomeric excess, respectively. The modified Mosher’s method was used to elucidate the absolute configuration of naturally occurring cudraisoflavone J.
AB - Cudraisoflavone J (1), isolated fromCudrania tricuspidata, is a potent neuroprotective compound with a chiral center. Herein, we report the first total synthesis of racemic cudraisoflavone J (1) using a Claisen rearrangement and a Suzuki coupling reaction as the key steps. Racemic secondary alcohol was kinetically resolved to give (+)- and (−)-cudraisoflavone J with up to 97 and 88% enantiomeric excess, respectively. The modified Mosher’s method was used to elucidate the absolute configuration of naturally occurring cudraisoflavone J.
UR - http://www.scopus.com/inward/record.url?scp=85105069054&partnerID=8YFLogxK
U2 - 10.1021/acs.jnatprod.1c00121
DO - 10.1021/acs.jnatprod.1c00121
M3 - Review article
C2 - 33826847
AN - SCOPUS:85105069054
SN - 0163-3864
VL - 84
SP - 1359
EP - 1365
JO - Journal of Natural Products
JF - Journal of Natural Products
IS - 4
ER -