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Synthesis of (−)-Berkelic Acid

Authors


  • We are grateful to the National Institutes of Health (GM-50151) for generous financial support. We thank Prof. D. Stierle for copies of spectral data of berkelic acid and berkelic acid methyl ester and Artem Shvartsbart for experimental assistance.

Abstract

An extremophilic challenge: Stereospecific condensation of a fully functionalized ketal aldehyde and a 2,6-dihydroxybenzoic acid is the key step in the synthesis of (−)-berkelic acid confirming Fürstner's reassignment of the stereochemistry at C18 and C19, establishing the absolute stereochemistry, and tentatively assigning the stereochemistry at C22.

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