Oxidative radical cyclizations of diketopiperazines bearing an amidomalonate unit. Heterointermediate reaction sequences toward the asperparalines and stephacidins
Jazyk angličtina Země Velká Británie, Anglie Médium print-electronic
Typ dokumentu časopisecké články
- Klíčová slova
- Alkaloids, diketopiperazines, oxidation, radical cyclizations, single electron transfer,
- MeSH
- alkaloidy chemie MeSH
- cyklizace MeSH
- diketopiperaziny chemie MeSH
- molekulární struktura MeSH
- oxidace-redukce MeSH
- Publikační typ
- časopisecké články MeSH
- Názvy látek
- alkaloidy MeSH
- diketopiperaziny MeSH
A novel approach to the diazabicyclo[2.2.2]octane core of prenylated bridged diketopiperazine alkaloids is described by direct oxidative cyclizations of functionalized diketopiperazines mediated by ferrocenium hexafluorophosphate or the Mn(OAc)3•2H2O/Cu(OTf)2 system. Divergent reaction pathways take place depending on the substitution pattern of the substrates and the oxidation conditions such as temperature or the presence or absence of persistent radical TEMPO. For ester-substituted diketopiperazines, the ester group exerts a significant influence on the reaction outcome and stereochemistry of the radical cyclizations.
Citace poskytuje Crossref.org
