Formal Synthesis of Hepatitis C Virus NS5B Polymerase Inhibitor

Noro, Takahiro; Okano, Kentaro; Tokuyama, Hidetoshi

doi:10.1055/s-0033-1339522

Cited by 5 publications

(1 citation statement)

References 2 publications

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“…The established cascade reaction terminated by S N 2 reaction was applied to a formal total synthesis of a hepatitis C virus (HCV) RNA polymerase inhibitor 40 14) (Chart 7). Chart 5.…”

Section: Introductionmentioning

confidence: 99%

Construction of <i>N</i>-Heterocycles Fused with a Highly Substituted Benzene Ring by a Benzyne-Mediated Cyclization/Functionalization Cascade Reaction and Its Application to the Total Synthesis of Marine Natural Products

Tokuyama

2021

Chem. Pharm. Bull.

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This account summarizes the development of a benzyne-mediated cyclization/functionalization protocol for the versatile construction of highly substituted benzene derivatives fused with an N-heterocyclic ring such as indolines, indoles, and related nitrogen-containing heterocycles. The protocol comprises sequential reactions initiated by generating a benzyne species and subsequent cyclization via addition of magnesium amide to the benzyne, followed by trapping of the resultant magnesium compound in situ with various electrophiles. The substituent scope was expanded by conducting a transmetalation on a copper species to introduce alkyl, aryl, and alkenyl substituents. The utility of the sequential reaction was demonstrated in the synthesis of a carbazole natural product (heptaphylline), pyrrolo[4,3,2-de]quinoline alkaloids (batzellines), and pyrrolo[2,3-c]carbazole alkaloids (dictyodendrines).

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“…The established cascade reaction terminated by S N 2 reaction was applied to a formal total synthesis of a hepatitis C virus (HCV) RNA polymerase inhibitor 40 14) (Chart 7). Chart 5.…”

Section: Introductionmentioning

confidence: 99%