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 product, including two pseudopericyclic cyclizations as well as a diastereoselective, hetero-Diels-Alder reaction.
Lumb
Jean-Philip
JP
Department of Chemistry, University of California, Berkeley, California 94720, United States. jplumb@stanford.edu
Krinsky
Jamin L
JL
Trauner
Dirk
D
D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D003500:Cyclization; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry; D008958:Models, Molecular; D015394:Molecular Structure; D009284:Naphthols / Q000138:chemical synthesis* / Q000737:chemistry; D010946:Plants, Medicinal / Q000737:chemistry; D011753:Pyrones / Q000138:chemical synthesis* / Q000737:chemistry; D045470:Rubia / Q000737:chemistry; D013237:Stereoisomerism
D001688:Biological Products; D005663:Furans; D009284:Naphthols; D011753:Pyrones; C102708:furomollugin; C499729:rubicordifolin