Total synthesis of antillatoxin, an ichthyotoxic cyclic lipopeptide from marine cyanobacterium Lyngbya majuscula

Citation
F. Yokokawa et T. Shioiri, Total synthesis of antillatoxin, an ichthyotoxic cyclic lipopeptide from marine cyanobacterium Lyngbya majuscula, J SYN ORG J, 58(7), 2000, pp. 634-641
Citations number
34
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN
ISSN journal
00379980 → ACNP
Volume
58
Issue
7
Year of publication
2000
Pages
634 - 641
Database
ISI
SICI code
0037-9980(200007)58:7<634:TSOAAI>2.0.ZU;2-B
Abstract
Antillatoxin is an ichthyotoxic cyclic lipopeptide isolated by Gerwick and co-workers from the marine cyanobacterium Lyngbya majuscula collected in Cu racao. Although we have finished the stereoselective total synthesis of ant illatoxin having the proposed structure with (4S, 5R)-configuration, we hav e found that the synthetic sample was not identical with the natural one an d the proposed structure should be revised. Further our synthetic efforts h ave culminated in the first total synthesis of antillatoxin in its natural form, proving that the natural one has (4R, 5R)-configuration. In this acco unt, our total synthesis and synthetic studies by other groups will be disc ussed.