4.7 Article

Atroposelective Total Syntheses of Naphthylisoquinoline Alkaloids with (P)-Configuration

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 85, Issue 19, Pages 12770-12776

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.0c01661

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Funding

  1. National Research Foundation of Korea (NRF) - Korean Government (Center for New Directions in Organic Synthesis) [NRF-2018R1D1A1A02086110, NRF-2020M2A8A4027369, NRF-2014-011165]

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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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