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Synfacts 2011(1): 0002-0002
DOI: 10.1055/s-0030-1259126
DOI: 10.1055/s-0030-1259126
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag
Stuttgart ˙ New York
Synthesis of (+)-Dictyosphaeric Acid A
Contributor(s):Steven V. Ley, Catherine F. CarterA. R. Burns, G. D. McAllister, S. E. Shanahan, R. J. K. Taylor*
University of York and GlaxoSmithKline, Tonbridge, UK
Total Synthesis and Structural Reassignment of (+)-Dictyosphaeric Acid A: A Tandem Intramolecular Michael Addition/Alkene Migration Approach
Angew. Chem. Int. Ed. 2010, 49: 5574-5577
University of York and GlaxoSmithKline, Tonbridge, UK
Total Synthesis and Structural Reassignment of (+)-Dictyosphaeric Acid A: A Tandem Intramolecular Michael Addition/Alkene Migration Approach
Angew. Chem. Int. Ed. 2010, 49: 5574-5577
Further Information
Publication History
Publication Date:
21 December 2010 (online)
Key words
(+)-dictyosphaeric acid A - intramolecular Michael addition - alkene migration
Significance
(+)-Dictyosphaeric acid A was isolated by Ireland and co-workers in 2004 from the green alga Dictyosphaeria versluyii. It was found to exhibit antibacterial activity against MRSA, Enterococcus faecium, and Candida albicans.
Comment
The key step of the synthesis is an intramolecular Michael addition followed by alkene migration to give H. The total synthesis allowed for the structural reassignment of the natural product and confirmation of the absolute configuration.