Synthesis of zanthoxyline and its related compounds: Revision of the reported structure

Hitoshi Abe; Naoko Kobayashi; Yasuo Takeuchi; Takashi Harayama

doi:10.3987/COM-09-S(S)111

Synthesis of zanthoxyline and its related compounds: Revision of the reported structure

Hitoshi Abe, Naoko Kobayashi, Yasuo Takeuchi, Takashi Harayama

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

17 Citations (Scopus)

Abstract

Benzo[c]phenanthridine alkaloid, zanthoxyline, was synthesized through an intramolecular biaryl coupling reaction of N-naphthylbenzamide derivative using a palladium reagent. Comparison of the NMR data for the synthetic product with that reported previously revealed that the proposed structure was incorrect. Synthesis of the related compounds suggested that the correct structure of zanthoxyline is the previously known decarine.

Original language	English
Pages (from-to)	873-877
Number of pages	5
Journal	Heterocycles
Volume	80
Issue number	2
DOIs	https://doi.org/10.3987/COM-09-S(S)111
Publication status	Published - Mar 1 2010

Keywords

Benzo[c]phenanthridine
Coupling Reaction
Palladium Catalyzed Reaction

ASJC Scopus subject areas

Analytical Chemistry
Pharmacology
Organic Chemistry

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10.3987/COM-09-S(S)111

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abstract = "Benzo[c]phenanthridine alkaloid, zanthoxyline, was synthesized through an intramolecular biaryl coupling reaction of N-naphthylbenzamide derivative using a palladium reagent. Comparison of the NMR data for the synthetic product with that reported previously revealed that the proposed structure was incorrect. Synthesis of the related compounds suggested that the correct structure of zanthoxyline is the previously known decarine.",

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author = "Hitoshi Abe and Naoko Kobayashi and Yasuo Takeuchi and Takashi Harayama",

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T2 - Revision of the reported structure

AU - Abe, Hitoshi

AU - Kobayashi, Naoko

AU - Takeuchi, Yasuo

AU - Harayama, Takashi

PY - 2010/3/1

Y1 - 2010/3/1

N2 - Benzo[c]phenanthridine alkaloid, zanthoxyline, was synthesized through an intramolecular biaryl coupling reaction of N-naphthylbenzamide derivative using a palladium reagent. Comparison of the NMR data for the synthetic product with that reported previously revealed that the proposed structure was incorrect. Synthesis of the related compounds suggested that the correct structure of zanthoxyline is the previously known decarine.

AB - Benzo[c]phenanthridine alkaloid, zanthoxyline, was synthesized through an intramolecular biaryl coupling reaction of N-naphthylbenzamide derivative using a palladium reagent. Comparison of the NMR data for the synthetic product with that reported previously revealed that the proposed structure was incorrect. Synthesis of the related compounds suggested that the correct structure of zanthoxyline is the previously known decarine.

KW - Benzo[c]phenanthridine

KW - Coupling Reaction

KW - Palladium Catalyzed Reaction

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JO - Heterocycles

JF - Heterocycles

IS - 2

ER -

Synthesis of zanthoxyline and its related compounds: Revision of the reported structure

Abstract

Keywords

ASJC Scopus subject areas

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