Total synthesis and revision of absolute stereochemistry of antillatoxin, an ichthyotoxic cyclic lipopeptide from marine cyanobacterium Lyngbya majuscula

Antillatoxin is an ichthyotoxic cyclic lipopeptide isolated by Gerwick and co-workers from the marine cyanobacterium Lyngbya majuscula collected in Curacao. 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. (C) 2000 Elsevier Science Ltd. All rights reserved.