Stellatolides, a New Cyclodepsipeptide Family from the Sponge Ecionemia acervus: Isolation, Solid-Phase Total Synthesis, and Full Structural Assignment of Stellatolide A

作者：Jesus Martin Maria; Rodriguez Acebes Raquel; Garcia Ramos Yesica; Martinez Valentin; Murcia Carmen; Digon Isabel; Marco Isabel; Pelay Gimeno Marta; Fernandez Rogelio; Reyes Fernando; Francesch Andres M; Munt Simon; Tulla Puche Judit^*; Albericio Fernando; Cuevas Carmen

来源：Journal of the American Chemical Society, 2014, 136(18): 6754-6762.

DOI：10.1021/ja502744a

The marine environment is a rich source of metabolites with potential therapeutic properties and applications for humans. Here we describe the first isolation, solid-phase total synthesis, and full structural assignment of a new class of cyclodepsipeptides from the Madagascan sponge Ecionemia acervus that shows in vitro cytotoxic activities at submicromolar concentrations. Seven structures belonging to a new family of compounds, given the general name stellatolides, were characterized. The sequence and stereochemistry of all the amino acids in these molecules were established by a combination of spectroscopic analysis, chemical degradation, and derivatization studies. Furthermore, the complete structure of stellatolide A was confirmed by an efficient solid-phase method for the first total synthesis and the full structural assignment of this molecule, including the asymmetric synthesis of the unique beta-hydroxy acid moiety (Z)-3-hydroxy-6,8-dimethylnon-4-enoic acid.

• 出版日期2014-5-7