Stereoselective synthesis of an advanced -decalin intermediate towards the total synthesis of anthracimycin

Progress towards the total synthesis of the macrolide natural product anthracimycin is described. This new approach utilises an intermolecular Diels-Alder strategy followed by epimeirsation to form the key trans -decalin framework. The route culminates in the stereoselective synthesis of an advanced...

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Published in:Chemical communications (Cambridge, England) England), 2024-05, Vol.6 (44), p.5699-572
Main Authors: Jeanmard, Laksamee, Lodovici, Giacomo, George, Ian, Bray, Joshua T. W, Whitwood, Adrian C, Thomas, Gavin H, Fairlamb, Ian J. S, Unsworth, William P, Clarke, Paul A
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Summary:Progress towards the total synthesis of the macrolide natural product anthracimycin is described. This new approach utilises an intermolecular Diels-Alder strategy followed by epimeirsation to form the key trans -decalin framework. The route culminates in the stereoselective synthesis of an advanced tricyclic lactone intermediate, containing five contiguous sterogenic centres with the correct relative and absolute stereochemistry required for the anthracimycin core motif. A stereoselective synthesis of an advanced trans -decalin intermediate towards the total synthesis of anthracimycin is described.
ISSN:1359-7345
1364-548X
DOI:10.1039/d4cc01738b