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Synfacts 2005(2): 0197-0197  
DOI: 10.1055/s-2005-916054
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Synthesis of (+)-Hippospongic Acid A

Contributor(s): Philip Kocienski, Fiona Black
B. M. Trost*, M. R. Machacek, H. C. Tsui
Stanford University, USA
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Publication History

Publication Date:
25 October 2005 (online)

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Significance

Hippospongic acid A is one of the few known inhibitors of gastrulation (differentiation of cell layers in the development of multicellular organisms) and would be useful in the study of organism development. This compound also shows modest inhibition of DNA polymerase and DNA topoisomerase I/II and it is active against the human gastric cancer cell line NUGC-3. The synthesis outlined above used Pd-catalyzed allylic alkylation reactions to construct three bonds (C-S, C-H, and C-O).