Theoretical Investigation of the Rubicordifolin Cascade

Theoretical Investigation of the Rubicordifolin Cascade

The results of a theoretical investigation on the complex cascade reaction leading to the natural product rubicordifolin are reported. These computations analyze the discrete transformations that are required during the conversion of the vinyl naphthoquinone starting material into the natural produc...

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Veröffentlicht in:Organic letters 2010-11, Vol.12 (22), p.5162-5165
Hauptverfasser: Lumb, Jean-Philip, Krinsky, Jamin L, Trauner, Dirk
Format: Artikel
Sprache:eng
Schlagworte:
Biological Products - chemical synthesis
Biological Products - chemistry
Catalysis
Cyclization
Furans - chemical synthesis
Furans - chemistry
Models, Molecular
Molecular Structure
Naphthols - chemical synthesis
Naphthols - chemistry
Plants, Medicinal - chemistry
Pyrones - chemical synthesis
Pyrones - chemistry
Rubia - chemistry
Stereoisomerism
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Beschreibung
Zusammenfassung:The results of a theoretical investigation on the complex cascade reaction leading to the natural product rubicordifolin are reported. These computations analyze the discrete transformations that are required during the conversion of the vinyl naphthoquinone starting material into the natural product, including two pseudopericyclic cyclizations as well as a diastereoselective, hetero-Diels−Alder reaction.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol102157d