Structure elucidation and spectroscopic analysis of photodegradants of the anti-rhinitis drug fluticasone furoate.
Fluticasone furoate is a novel glucocorticoid receptor agonist marketed as a treatment for seasonal and perennial allergic rhinitis. Forced degradation of fluticasone furoate under conditions of light led to a number of degradation products, the structures of which were elucidated using mass spectrometry and a range of one and two-dimensional NMR experiments. Three structures were derived, including two which involved a rearrangement of the steroid ring A to give cross-linked degradation products. The results demonstrate the applicability of a previously observed mechanism of photodegradation to fluticasone furoate.
Palladium(0)-catalyzed [2 + 2 + 1] cyclization of 1,6-enynes with vinyl bromides: a highly diastereoselective synthesis of tetrahydro-1H-cyclopenta[c]furans bearing two quaternary carbon centers.
A new cascade process has been accomplished for the synthesis of tetrahydro-1H-cyclopenta[c]furans through palladium-catalyzed [2 + 2 + 1] cyclization of 1,6-enynes with vinyl bromides. Notably, the key feature of this transformation is the use of vinyl bromides as the C1 building block. Various functionalized tetrahydro-1H-cyclopenta[c]furans bearing two quaternary carbon centers could be obtained in good yields with excellent diastereoselectivities.
Lupin alkaloids from teratogenic and nonteratogenic lupins. II. Identification of the major alkaloids by tandem gas chromatography-mass spectrometry in plants producing crooked calf disease.
The major alkaloids of lupin plants producing crooked calf disease were identified by tandem gas chromatography-mass spectrometry and infrared analysis. The gas chromatography peak invariably present in teratogenic plants proved to be anagyrine. A minor but irregular contaminant of the peak was α-isolupanine. Other alkaloids present but apparently not associated with crooked calf disease were lupanine and two others that were probably epimethoxylupanine and 5,6-dehydrolupanine.