Solvolysis of 14,17-etheno-bridged 16alpha-nitroestratrienyl acetate and lactam 
formation pathways studied by LC-NMR and LC-MS. Structures of minor products

Baranovsky, Alexander; Bolibrukh, Dmitry A.; Schneider, Bernd

doi:10.1016/j.steroids.2015.08.009

Datensatz

DATENSATZ AKTIONENEXPORT

Zur Ablage hinzufügen

Lokale TagsFreigabegeschichteDetailsÜbersicht

Freigegeben

Zeitschriftenartikel

Solvolysis of 14,17-etheno-bridged 16alpha-nitroestratrienyl acetate and lactam formation pathways studied by LC-NMR and LC-MS. Structures of minor products

MPG-Autoren

/persons/resource/persons4159

Schneider, Bernd
Research Group Biosynthesis / NMR, MPI for Chemical Ecology, Max Planck Society;

Externe Ressourcen

Es sind keine externen Ressourcen hinterlegt

Volltexte (beschränkter Zugriff)

Für Ihren IP-Bereich sind aktuell keine Volltexte freigegeben.

Volltexte (frei zugänglich)

Es sind keine frei zugänglichen Volltexte in PuRe verfügbar

Ergänzendes Material (frei zugänglich)

Es sind keine frei zugänglichen Ergänzenden Materialien verfügbar

Zitation

Baranovsky, A., Bolibrukh, D. A., & Schneider, B. (2015). Solvolysis of 14,17-etheno-bridged 16alpha-nitroestratrienyl acetate and lactam formation pathways studied by LC-NMR and LC-MS. Structures of minor products. Steroids, 104, 37-48. doi:10.1016/j.steroids.2015.08.009.

Zitierlink: https://hdl.handle.net/11858/00-001M-0000-0028-3559-0

Zusammenfassung

The ethanol solvolysis of 3-methoxy-14,17-etheno-16a-nitroestra-1,3,5(10)-trien-17b-yl acetate in the
presence of NaHCO3 was studied by means of real-time NMR experiments, LC–SPE–NMR, and LC–MS.
The pathway to form 3-methoxy-20-oxopyrrolidino-[40,50:14b,15b]-estra-1,3,5(10)-trien-17-one was
disclosed. The intermediacy of nitrile oxide and alkoxynitrone was postulated based on the analysis of
the reaction products. The proposed mechanism of cleaving the bridge in the nitro compound is legal
for the formation of N-acetoxylactams, nitriles, isoxazoles and isoxazolines.