Synthesis of (±)-Demethylnitidanin, Herpetol and Salvinal as well as Their Glycosyl Derivatives

高等学校化学研究 ›› 2011, Vol. 27 ›› Issue (6): 949-954.

Synthesis of (±)-Demethylnitidanin, Herpetol and Salvinal as well as Their Glycosyl Derivatives

WU Zheng, LIANG Zhi-ying, LI Wei, REN Ying-mei and WANG Qiu-an*

State Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082, P. R. China

收稿日期:2011-01-21 修回日期:2011-03-30 出版日期:2011-11-25 发布日期:2011-11-07
通讯作者: WANG Qiu-an E-mail:WangQA@hnu.edu.cn
基金资助:
Supported by the Personal Training Funds in National Basic Science of China(No.J0830415).

Synthesis of Naturally Occurring Neolignans Demethylnitidanin, Herpetol and Salvinal as well as Their Glycosyl Derivatives

WU Zheng, LIANG Zhi-ying, LI Wei, REN Ying-mei and WANG Qiu-an*

State Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082, P. R. China

Received:2011-01-21 Revised:2011-03-30 Online:2011-11-25 Published:2011-11-07
Contact: WANG Qiu-an E-mail:WangQA@hnu.edu.cn
Supported by:
Supported by the Personal Training Funds in National Basic Science of China(No.J0830415).

摘要/Abstract

摘要： Three neolignans, (±)-demethylnitidanin(1), herpetol(2) and salvinal(3) were synthesized from methyl 4,5-dihydroxy-3-methoxy cinnamate or methyl 4-hydroxy-3-methoxy cinnamate with Ag2O-catalyzed biomimetic oxidative coupling as the key step of the synthetic route. Five novel benzofuran neolignan-4'-O-β-D-glycosides(4―8) were achieved by the glycosylation reactions of benzofuran neolignans 2, 3 and 15. The structures of all the compounds synthesized were determined by MS, 1H NMR and IR spectra. (±)-Demethylnitidanin(1) and herpetol(2) were the first synthesized and the synthesis of salvinal(3) was efficiently improved by the new synthetic routes.

关键词: Neolignan, (±)-Demethylnitidanin, Herpetol, Salvinal, Glycosylation

Abstract: Three neolignans, (±)-demethylnitidanin(1), herpetol(2) and salvinal(3) were synthesized from methyl 4,5-dihydroxy-3-methoxy cinnamate or methyl 4-hydroxy-3-methoxy cinnamate with Ag2O-catalyzed biomimetic oxidative coupling as the key step of the synthetic route. Five novel benzofuran neolignan-4'-O-β-D-glycosides(4―8) were achieved by the glycosylation reactions of benzofuran neolignans 2, 3 and 15. The structures of all the compounds synthesized were determined by MS, 1H NMR and IR spectra. (±)-Demethylnitidanin(1) and herpetol(2) were the first synthesized and the synthesis of salvinal(3) was efficiently improved by the new synthetic routes.

Key words: Neolignan, (±)-Demethylnitidanin, Herpetol, Salvinal, Glycosylation

WU Zheng, LIANG Zhi-ying, LI Wei, REN Ying-mei and WANG Qiu-an*. Synthesis of (±)-Demethylnitidanin, Herpetol and Salvinal as well as Their Glycosyl Derivatives[J]. 高等学校化学研究, 2011, 27(6): 949-954.

WU Zheng, LIANG Zhi-ying, LI Wei, REN Ying-mei and WANG Qiu-an*. Synthesis of Naturally Occurring Neolignans Demethylnitidanin, Herpetol and Salvinal as well as Their Glycosyl Derivatives[J]. Chemical Research in Chinese Universities, 2011, 27(6): 949-954.

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