Total Synthesis of (-)-Piericone D.

Yuan, Shaopan; Pei, Wanqing; Di, Xuan; Qin, Yali; Jin, Hongming; Meng, Zhanchao; Hou, Xiaoli

Yuan, Shaopan; Pei, Wanqing; Di, Xuan; Qin, Yali; Jin, Hongming; Meng, Zhanchao; Hou, Xiaoli.

Afiliação

Yuan S; School of Pharmacy, Nanjing University of Chinese Medicine, Nanjing 210023, China.
Pei W; Lingang Lab, Shanghai 200031, China.
Di X; School of Pharmacy, Nanjing University of Chinese Medicine, Nanjing 210023, China.
Qin Y; Lingang Lab, Shanghai 200031, China.
Jin H; School of Pharmacy, Nanjing University of Chinese Medicine, Nanjing 210023, China.
Meng Z; School of Pharmacy, Nanjing University of Chinese Medicine, Nanjing 210023, China.
Hou X; School of Pharmacy, Nanjing University of Chinese Medicine, Nanjing 210023, China.

J Org Chem ; 89(12): 8782-8788, 2024 Jun 21.

Article em En | MEDLINE | ID: mdl-38819141

ABSTRACT

ABSTRACT

The total synthesis of (-)-piericone D, a potential antithrombotic dihydrochalcone featuring an [3.3.0] octane core, is reported. Salient features of our synthesis include a stereoselective ß-O-glycosylation to install the asebogenin aglycone and a late-stage global deprotection followed by simultaneous lactonization. The convergent synthesis paved the way for further structure-activity relationship (SAR) studies of (-)-piericone D.

Assuntos

Chalconas; Estereoisomerismo; Chalconas/química; Chalconas/síntese química; Estrutura Molecular; Glicosilação; Relação Estrutura-Atividade

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Texto completo: 1 Coleções: 01-internacional Base de dados: MEDLINE Assunto principal: Chalconas Idioma: En Revista: J Org Chem Ano de publicação: 2024 Tipo de documento: Article País de afiliação: China País de publicação: Estados Unidos

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