Total Synthesis of the Neuroprotective Agent Cudraisoflavone J

Qili Lu; Dipesh S. Harmalkar; Guofeng Quan; Haeun Kwon; Jungsook Cho; Yongseok Choi; Dongho Lee; Kyeong Lee

doi:10.1021/acs.jnatprod.1c00121

Total Synthesis of the Neuroprotective Agent Cudraisoflavone J

Qili Lu
, Dipesh S. Harmalkar
, Guofeng Quan
, Haeun Kwon
, Jungsook Cho
, Yongseok Choi
, Dongho Lee
, Kyeong Lee^*

^*Corresponding author for this work

Research output: Contribution to journal › Review article › peer-review

9 Citations (Scopus)

Abstract

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.

Original language	English
Pages (from-to)	1359-1365
Number of pages	7
Journal	Journal of Natural Products
Volume	84
Issue number	4
DOIs	https://doi.org/10.1021/acs.jnatprod.1c00121
Publication status	Published - 2021 Apr 23

Bibliographical note

Publisher Copyright:
© 2021 American Chemical Society and American Society of Pharmacognosy

ASJC Scopus subject areas

Analytical Chemistry
Molecular Medicine
Pharmacology
Pharmaceutical Science
Drug Discovery
Complementary and alternative medicine
Organic Chemistry

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10.1021/acs.jnatprod.1c00121

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title = "Total Synthesis of the Neuroprotective Agent Cudraisoflavone J",

abstract = "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{\textquoteright}s method was used to elucidate the absolute configuration of naturally occurring cudraisoflavone J.",

author = "Qili Lu and Harmalkar, \{Dipesh S.\} and Guofeng Quan and Haeun Kwon and Jungsook Cho and Yongseok Choi and Dongho Lee and Kyeong Lee",

note = "Publisher Copyright: {\textcopyright} 2021 American Chemical Society and American Society of Pharmacognosy",

year = "2021",

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doi = "10.1021/acs.jnatprod.1c00121",

language = "English",

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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

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 - https://www.scopus.com/pages/publications/85105069054

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 -

Total Synthesis of the Neuroprotective Agent Cudraisoflavone J

Abstract

Bibliographical note

ASJC Scopus subject areas

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