Atroposelective Total Syntheses of Naphthylisoquinoline Alkaloids with (P)-Configuration
- Authors
- Jo, Young-In; Lee, Chun-Young; Cheon, Cheol-Hong
- Issue Date
- 2-10월-2020
- Publisher
- AMER CHEMICAL SOC
- Citation
- JOURNAL OF ORGANIC CHEMISTRY, v.85, no.19, pp.12770 - 12776
- Indexed
- SCIE
SCOPUS
- Journal Title
- JOURNAL OF ORGANIC CHEMISTRY
- Volume
- 85
- Number
- 19
- Start Page
- 12770
- End Page
- 12776
- URI
- https://scholar.korea.ac.kr/handle/2021.sw.korea/52496
- DOI
- 10.1021/acs.joc.0c01661
- ISSN
- 0022-3263
- 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-(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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