Marine tricyclic alkaloids lepadiformine and fasicularin, with
a unique perhydropyrrolo[2,1-j]quinoline or perhydropyrido[2,1-j]quinoline framework, were synthesized starting from the
B ring of the tricyclic system. This approach includes a highly stereocontrolled
diallylation of a cyclic enaminoester and subsequent ring-closing
metathesis to construct the A/B ring system, which was transformed
into key lactams 32 and 33, and amino alcohol 37. Thus, we achieved formal syntheses of (−)-lepadiformines
A, C, and (−)-fasicularin in a divergent manner.
Lewis acid‐catalyzed [6+1] annulation reactions of 2‐cyano‐1‐propargyl‐ and 2‐alkynyl‐1‐cyanomethyl‐indoles with Reformatsky reagent are described. 8‐Aryl, 8‐alkyl‐, 8‐hetaryl‐, 9‐aryl, and 9‐alkyl‐azepino[1,2‐a]indole amines were obtained through a 7‐endo‐mode cyclization of the β‐aminoacrylate intermediates. The antiproliferative activity of the azepino[1,2‐a]indoles analogs against the HCT‐116 cells were also examined.
A major challenge in fluorescence imaging experiments, which are essential to determine protein activity, expression, and localization, is the penetration of small-molecule probes through the outer membrane permeability barrier of...
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