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Synfacts 2009(8): 0825-0825  
DOI: 10.1055/s-0029-1217507
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of (-)-Berkelic Acid

Contributor(s): Philip Kocienski, Indu Dager
X. Wu, J. Zhou, B. B. Snider*
Brandeis University, Waltham, USA
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Publication History

Publication Date:
23 July 2009 (online)

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Significance

Berkelic acid is a metabolite of a fungal extremophile, thriving on acid mine waste, that inhibits MMP-3 and caspase-1. It also shows selective activity toward ovarian cancer OVCAR-3 (GI50 91 nM). A stereo­specific condensation between the ketal aldehyde D and dihydroxybenzoic acid E to construct tetracyclic core F is the focal step of the synthesis confirming the reassignment of configurations at C-18 and C-19 by Fürstner (Angew. Chem. Int. Ed. 2008, 47, 8450) and also tentatively assigning the stereochemistry at C-22.