Pericyclic reactions of prenylated naphthoquinones: biomimetic syntheses of mollugin and microphyllaquinone.
[reaction: see text] A total synthesis of the bioactive naphthohydroquinone mollugin and the related naphthoquinone dimer microphyllaquinone is described. Both syntheses exploit the propensity of prenylated quinones to undergo tautomerization/oxa 6pi-electrocyclizations.
Lumb
Jean-Philip
JP
Department of Chemistry, University of California, Berkeley, California 94720, USA.
Trauner
Dirk
D
D003500:Cyclization; D015394:Molecular Structure; D009285:Naphthoquinones / Q000138:chemical synthesis* / Q000737:chemistry*; D010946:Plants, Medicinal / Q000737:chemistry; D011714:Pyrans / Q000138:chemical synthesis* / Q000737:chemistry; D045470:Rubia / Q000737:chemistry; D013237:Stereoisomerism
D009285:Naphthoquinones; D011714:Pyrans; C513050:microphyllaquinone; C046245:rubimaillin