Yamu Xia,Chenglong Chen,Mengying Li,Weizeng Zhou,Shuyu Sun,Shanpeng Chu,Hui Wang
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.
Lijing Fang,Chunlei Wu,Zaidan Yu,Peng Shang,Yongxian Cheng,Yuefeng Peng,Wu Su
Graphical A highly efficient protocol for the triphosgene-mediated solid-phase coupling of proteinogenic amino acids is developed and applied to the first total synthesis of the bioactive natural octacyclopeptide brachystemin A. A reproducible, highly efficient, and racemization-free protocol for the triphosgene-mediated solid-phase coupling of proteinogenic amino acids was developed. The efficiency of the reaction was demonstrated by the first total synthesis of the bioactive natural octacyclopeptide brachystemin A. This protocol will broaden the application of triphosgene in the synthesis of a wide range of peptides, including aromatic amino acids, N -alkylated amino acids, as well as proteinogenic amino acids.