AI Article Synopsis
- The article details a successful method for synthesizing berkelic acid, highlighting its biological significance.
- The synthesis faced challenges, especially in adding the C-18 methyl group and required exploring multiple strategies to achieve the correct stereochemistry.
- Ultimately, a specific reaction sequence involving a silyl enol ether and subsequent transformations yielded the desired tetracyclic structure as a single diastereoisomer.
Article Abstract
The full details of our enantioselective formal synthesis of the biologically active natural product berkelic acid are described. The insertion of the C-18 methyl group proved challenging, with three different approaches investigated to install the correct stereochemistry. Our initial Horner-Wadsworth-Emmons/oxa-Michael approach to the berkelic acid core proved unsuccessful upon translation to the natural product itself. However, addition of a silyl enol ether to an oxonium ion, followed by a one-pot debenzylation/spiroketalisation/thermodynamic equilibration procedure, afforded the tetracyclic structure of the berkelic acid core as a single diastereoisomer.
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| http://dx.doi.org/10.1021/jo201988m | DOI Listing |
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