Total Synthesis of (+)-Euphorikanin A via an Atropospecific Cascade

A total synthesis of the ingenane-derived diterpenoid (+)-euphorikanin A is described. Key to the strategy is a stereocontrolled one-pot sequence consisting of transannular aldol addition reaction, hemiketal formation, and subsequent semipinacol rearrangement that efficiently leads to the complete e...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2023-12, Vol.145 (50), p.27225-27229
Main Authors: Classen, Moritz J., Kicin, Bilal, Ruf, Vincent A. P., Hamminger, Alexander, Ribadeau-Dumas, Loélie, Amberg, Willi M., Carreira, Erick M.
Format: Article
Language:English
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Summary:A total synthesis of the ingenane-derived diterpenoid (+)-euphorikanin A is described. Key to the strategy is a stereocontrolled one-pot sequence consisting of transannular aldol addition reaction, hemiketal formation, and subsequent semipinacol rearrangement that efficiently leads to the complete euphorikanin skeleton. Atroposelective ring-closing olefin metathesis proved critical for the stereospecific cascade, leading to formation of a (Z)-bicyclo­[7.4.1]­tetradecenone core. An additional salient feature of the route is pyrolysis of a bis-methylxanthate to cleanly furnish the natural product.
ISSN:0002-7863
1520-5126
DOI:10.1021/jacs.3c11000