Atroposelective Total Syntheses of Naphthylisoquinoline Alkaloids with P-Configuration.

Asymmetric total syntheses of naphthylisoquinoline alkaloids with a P-configuration are described. An atroposelective Suzuki-Miyaura reaction between naphthyl pinacol boronate and an aryl iodide bearing an (S)-2-(N-acetylamino)propyl group at the ortho-position, using Pd(OAc)2 in the presence of SPhos and Ba(OH)2 provided the P-selective biaryl product as the major product, without any external chiral sources. This biaryl product was converted into naphthylisoquinoline alkaloids with a P-configuration via stereoselective construction of the isoquinoline framework with the appropriate oxidation state and stereochemistry.

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