Abstract
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.
Original language | English |
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Pages (from-to) | 12770-12776 |
Number of pages | 7 |
Journal | Journal of Organic Chemistry |
Volume | 85 |
Issue number | 19 |
DOIs | |
Publication status | Published - 2020 Oct 2 |
ASJC Scopus subject areas
- Organic Chemistry