Synthesis of polycarpine, a cytotoxic sulfur-containing alkaloid from the ascidian Polycarpa aurata, and related compounds

✍ Scribed by Oleg S. Radchenko; Vyacheslav L. Novikov; Richard H. Willis; Peter T. Murphy; George B. Elyakov

• Book ID: 104257032
• Publisher: Elsevier Science
• Year: 1997
• Tongue: French
• Weight: 221 KB
• Volume: 38
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(97)00668-0

✦ Synopsis

Polycarpine 1, a highly cytotoxic marine natural product, has been synthesized in three steps from p-metho..xyphenacyl bromide 4_ in 57% overall yield. The key reaction for construction of the synunetrically substituted disulfide linkage of polycarpine is the treatment of 2-amino-4-(4-methox3~phenyl)-l-methylimidazole 1"7 with $2C1~ in acetic acid. In a similar way ten related compounds, including three thiazole analogues, have been prepared. Most of them exhibit high cytotoxic activities against an array of human cancer cell lines.