ChemInform Abstract: Total Synthesis of Motuporin and 5-[L-Ala]-Motuporin.

✍ Scribed by Raghu Samy; Hong Yong Kim; Matthew Brady; Peter L. Toogood

• Publisher: John Wiley and Sons
• Year: 2010
• Weight: 29 KB
• Volume: 30
• Category: Article
• ISSN: 0931-7597
• DOI: 10.1002/chin.199936218

✦ Synopsis

Total Synthesis of Motuporin and 5-[L-Ala]-Motuporin.

-Three strategies to motuporin (I) are outlined with their relative strengths and weaknesses, but none of the approaches are entirely satisfactory. In each case, the purification of the final product following saponification of the methyl esters, appearing with multiple side reactions, represents a major difficulty. 5-[L-Ala]-Motuporin (II) is prepared from its dimethyl ester and the yields for all except the final two steps are generally better than for motuporin. The synthetic cyclic pentapeptide (II) is a potent inhibitor of PP1, indicating that motuporin analogues lacking the dehydroamino acid should retain inhibitory activity against protein phosphatases.