Atroposelective total syntheses of naphthylisoquinoline alkaloids with (p)-configuration

Cheol Hong Cheon; Young In Jo; Chun Young Lee

doi:10.1021/acs.joc.0c01661

Atroposelective total syntheses of naphthylisoquinoline alkaloids with (p)-configuration

Cheol Hong Cheon, Young In Jo, Chun Young Lee

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

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
Pages (from-to)	12770-12776
Number of pages	7
Journal	Journal of Organic Chemistry
Volume	85
Issue number	19
DOIs	https://doi.org/10.1021/acs.joc.0c01661
Publication status	Published - 2020 Oct 2

ASJC Scopus subject areas

Organic Chemistry

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title = "Atroposelective total syntheses of naphthylisoquinoline alkaloids with (p)-configuration",

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.",

author = "Cheon, {Cheol Hong} and Jo, {Young In} and Lee, {Chun Young}",

note = "Funding 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).",

year = "2020",

month = oct,

day = "2",

doi = "10.1021/acs.joc.0c01661",

language = "English",

volume = "85",

pages = "12770--12776",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "19",

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TY - JOUR

T1 - Atroposelective total syntheses of naphthylisoquinoline alkaloids with (p)-configuration

AU - Cheon, Cheol Hong

AU - Jo, Young In

AU - Lee, Chun Young

N1 - Funding 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).

PY - 2020/10/2

Y1 - 2020/10/2

N2 - 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.

AB - 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.

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JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

SN - 0022-3263

IS - 19

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Atroposelective total syntheses of naphthylisoquinoline alkaloids with (p)-configuration

Abstract

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