Chemoenzymatic formal synthesis of (+)-brazilin.

Herein, the manuscript presents a chemoenzymatic formal synthetic route of (+)-brazilin, a homoisoflavonoid natural product with a chroman skeleton cis-fused with a 2,3-dihydro-1H-indene unit, which is isolated from the traditional Chinese medicine, Caesalpinia sappan L. The key feature of the synth...

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Bibliographic Details
Published in:Natural Product Research
Main Authors: Liu, Jiangtao, Han, Xue, Yu, Liuping, Zhang, Jiandong, Huang, Shuangping, Yang, Xihua, Chang, Honghong
Format: Article in Journal/Newspaper
Language:English
Published: Atypon 2024
Subjects:
(+)-brazilin
CALB lipase
Natural product
chemoenzymatic synthesis
desymmetrization
Antarc*
Antarctica
Online Access:https://doi.org/10.1080/14786419.2024.2349255
https://pubmed.ncbi.nlm.nih.gov/38712549
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Summary:Herein, the manuscript presents a chemoenzymatic formal synthetic route of (+)-brazilin, a homoisoflavonoid natural product with a chroman skeleton cis-fused with a 2,3-dihydro-1H-indene unit, which is isolated from the traditional Chinese medicine, Caesalpinia sappan L. The key feature of the synthetic strategy includes an enzyme-mediated desymmetrization by employing lipase from Candida antarctica type B (CALB) and a one-pot SN2/hydrolysis reaction.

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