Bioinspired Total Synthesis of (+)-Euphorikanin A
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION(2022)
Abstract
We have achieved a bioinspired total synthesis of (+)-euphorikanin A, which possesses an intriguing and complex 5/6/7/3-fused tetracyclic skeleton bearing a bridged [3.2.1]-gamma-lactone moiety. Key transformations include stereoselective alkylation and aldol condensation to install the main stereocenters, an intramolecular nucleophile-catalyzed aldol lactonization of carboxylic acid-ketone to assemble the five-membered ring, a McMurry coupling to construct the seven-membered ring, and a biomimetic benzilic acid type rearrangement to form the bridged [3.2.1]-gamma-lactone moiety.
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Key words
Asymmetric Synthesis, Bioinspired Synthesis, Natural Products, Terpenoids, Total Synthesis
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