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-(Nacetylamino) 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.
Bibliographical noteFunding Information:
This work was supported by the National Research Foundation of Korea (NRF) grants funded by the Korean Government (NRF-2018R1D1A1A02086110, NRF-2020M2A8A4027369, and NRF-2014-011165, Center for New Directions in Organic Synthesis).
ASJC Scopus subject areas
- Organic Chemistry