Total Synthesis and Revision of Absolute Stereochemistry of Antillatoxin, an Ichthyotoxic Cyclic Lipopeptide from Marine Cyanobacterium Lyngbya majuscula

✍ Scribed by Fumiaki Yokokawa; Hideyasu Fujiwara; Takayuki Shioiri

• Book ID: 104202549
• Publisher: Elsevier Science
• Year: 2000
• Tongue: French
• Weight: 351 KB
• Volume: 56
• Category: Article
• ISSN: 0040-4020
• DOI: 10.1016/s0040-4020(00)00081-8

✦ Synopsis

Antillatoxin is an ichthyotoxic cyclic lipopeptide isolated by Gerwick and co-workers from the marine cyanobacterium Lyngbya majuscula collected in Curac ¸ao. Although we have finished the stereoselective total synthesis of antillatoxin having the proposed structure with (4S,5R)-configuration, we have found that the synthetic sample was not identical with the natural one and the proposed structure should be revised. Further our synthetic efforts have culminated in the first total synthesis of antillatoxin in its natural form, proving that the natural one has (4R,5R)-configuration.