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A bioinspired convergent total synthesis of (+)‐haplophytine, a dimeric indole alkaloid with diazabicyclo[3.3.1]nonane and hexacyclic aspidosperma segments, is described. This synthesis involves the direct coupling of the two segments in a AgNTf2‐mediated Friedel–Crafts reaction and construction of the diazabicyclo[3.3.1]nonane skeleton through late‐stage chemoselective aerobic oxidation of the 1,2‐diaminoethene...
Der Schlüsselschritt in dieser Totalsynthese von (−)‐Acetylaranotin ist die effiziente Bildung des charakteristischen Dihydrooxepinrings aus Cyclohexenon durch eine ungewöhnliche vinyloge Rubottom‐Oxidation und regioselektive Baeyer‐Villiger‐Oxidation. (−)‐Acetylaranotin wurde in 22 Stufen aus kommerziell erhältlichem L‐Cbz‐Tyrosin (Cbz=Benzyloxycarbonyl) erhalten.
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