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DOI: 10.1055/s-0029-1218259
Synthesis of Berkelic Acid
Contributor(s):Philip KocienskiUniversity of Texas Southwestern Medical Center at Dallas, USA
A Concise Synthesis of Berkelic Acid Inspired by Combining the Natural Products Speciferin and Pulvilloric Acid
J. Am. Chem. Soc. 2009, 131: 11350-11352
Publication History
Publication Date:
21 December 2009 (online)
Key words
berkelic acid - cycloisomerization - Diels-Alder reaction - ortho-quinone methides
Significance
Berkelic acid is a metabolite of an extremophilic Penicillium fungus. It displays activity against the human ovarian cancer cell line OVCAR-3 and moderate inhibition of matrix metalloproteinase MMP-3 and caspase-1. The synthesis depicted features a silver-catalyzed dearomatization-cycloisomerization-cycloaddition cascade to create the spiroacetal.
Comment
The sequence depicted in the Scheme used a mixture of diastereoisomers Aa and Ab (6:4) and the resultant mixture of cycloadducts was subsequently separated. The difficult selective hydrolysis of the benzoate ester was accomplished by heating E with a large excess of (Bu3Sn)2O.