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Synfacts 2006(8): 0748-0748  
DOI: 10.1055/s-2006-941937
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Synthesis and Structural Elucidation of Azaspiracid-1

Contributor(s): Philip Kocienski, Thomas Snaddon
K. C. Nicolaou*, T. V. Koftis, S. Vyskocil, G. Petrovic, W. Tang, M. O. Frederick, D. Y.-K. Chen, T. Ling, Y. Li, Y. M. A. Yamada
The Scripps Research Institute and Universtiy of California, La Jolla, USA
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Publikationsdatum:
21. Juli 2006 (online)

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Significance

Azaspiracid-1 is isolated from mussels (Mytilus edulis). It causes nausea, vomiting and diarrhea with damage to the liver and spleen and it induces the formation of lung tumors in mice. This paper details the synthesis of the correct structure of azaspiracid-1 by (1) the deft use of ring-closing cascade reactions to assemble the ABCD and FHI ring systems and (2) the use of a Stille coupling as a mild late-stage fragment linkage method.