First total synthesis of mariamide A. Issue 1 (January 2020)

• Record Type: Journal Article
• Authors: Xia, Yamu; Chen, Chenglong; Li, Mengying; Zhou, Weizeng; Sun, Shuyu; Chu, Shanpeng; Wang, Hui
• Is Part Of: Journal of chemical research. Volume 44:Issue 1/2(2020)
• Page Start: 114
• Page End: 120
• Publication Date: 2020-01
• Subjects: 8-O-4′ neolignans -- I2-catalyzed bromomethoxylation -- lignanamides -- mariamide A -- lignans; Chemistry -- Research -- Periodicals; Chemistry -- Periodicals; 540.5
• DOI: 10.1177/1747519819890821
• Languages: English
• ISSNs: 1747-5198

Abstract

Mariamide A, a lignanamide isolated from the seeds of Silybum marianum, has demonstrated potential utility as an antioxidant and antidiabetic agent and possesses an 8-O-4′ neolignan skeleton. Herein, a first total synthesis of mariamide A is presented that proceeds in nine steps using vanillin as the starting material. The key steps for the preparation of mariamide A involve an I2 -catalyzed bromomethoxylation of an alkene group, a nucleophilic substitution followed by a sequential elimination and a monoacylation reaction.