Organic solvent nanofiltration
(OSN) promises to be a versatile
tool for mild and energy-saving downstream processing. In this case
study, the use of modern solvent-resistant membranes to separate organocatalysts
from reaction media was investigated. Commercially available membranes
with molecular weight cut-offs (MWCOs) between 150 and 500 g mol–1 were used. They showed high rejections of up to 99%
for native catalysts in THF. The enantioselective Henry reaction of
ethyl pyruvate and nitromethane catalyzed by benzoyl cupreine was
used to demonstrate the potential of this technique for preparative
use.
Selenoindirubins and selenoindirubin-N-glycosides were prepared by the reaction of isatins and isatin-N-glycosides with 3-acetoxy-benzo[b]selenophene, respectively. While selenoindirubin-N-glycosides have not been reported before, three non-glycosylated selenoindirubins were previously reported, but without quantities, yields, scales, experimental details and spectroscopic data. In addition, the work could, in our hands, not be reproduced to prepare pure products. The present paper includes an optimized procedure for the synthesis of selenoindirubins and their complete characterization. Both selenoindirubins and selenoindirubin-N-glycosides showed antiproliferative activity in lung cancer cell lines. In melanoma cells, antiproliferative effects were further accompanied by induced apoptosis in combination with the death ligand TRAIL.
Octahydro-indeno-phenanthrenes, benzo-annulated steroids, were prepared by formal [3 þ 3] cyclocondensation reaction of 1,3-bis[(trimethylsilyl)oxy]buta-1,3-dienes with the silyl enol ether of 16formylestrone methyl ether.
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