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

Stereoselective synthesis of an advanced trans -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 -decalin framework. The route culminates in the stereoselective synthesis of an advanced tricy...

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Veröffentlicht in:Chemical communications (Cambridge, England) England), 2024-05, Vol.60 (44), p.5699-5702
Hauptverfasser: 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
Format: Artikel
Sprache:eng
Schlagworte:
Chemistry
Decalin
Natural products
Stereochemistry
Stereoselectivity
Synthesis
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Zusammenfassung: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 -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.
ISSN:1359-7345
1364-548X
DOI:10.1039/d4cc01738b