Synthesis of zanthoxyline and its related compounds

Revision of the reported structure

Hitoshi Abe, Naoko Kobayashi, Yasuo Takeuchi, Takashi Harayama

Research output: Contribution to journalArticle

14 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 languageEnglish
Pages (from-to)873-877
Number of pages5
JournalHeterocycles
Volume80
Issue number2
DOIs
Publication statusPublished - Mar 1 2010

Fingerprint

Phenanthridines
Palladium
Alkaloids
Nuclear magnetic resonance
Derivatives

Keywords

  • Benzo[c]phenanthridine
  • Coupling Reaction
  • Palladium Catalyzed Reaction

ASJC Scopus subject areas

  • Analytical Chemistry
  • Organic Chemistry
  • Pharmacology

Cite this

Synthesis of zanthoxyline and its related compounds : Revision of the reported structure. / Abe, Hitoshi; Kobayashi, Naoko; Takeuchi, Yasuo; Harayama, Takashi.

In: Heterocycles, Vol. 80, No. 2, 01.03.2010, p. 873-877.

Research output: Contribution to journalArticle

Abe, Hitoshi ; Kobayashi, Naoko ; Takeuchi, Yasuo ; Harayama, Takashi. / Synthesis of zanthoxyline and its related compounds : Revision of the reported structure. In: Heterocycles. 2010 ; Vol. 80, No. 2. pp. 873-877.
@article{fcaf998ac4cf415d9ffb8ec9efbd636c,
title = "Synthesis of zanthoxyline and its related compounds: Revision of the reported structure",
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.",
keywords = "Benzo[c]phenanthridine, Coupling Reaction, Palladium Catalyzed Reaction",
author = "Hitoshi Abe and Naoko Kobayashi and Yasuo Takeuchi and Takashi Harayama",
year = "2010",
month = "3",
day = "1",
doi = "10.3987/COM-09-S(S)111",
language = "English",
volume = "80",
pages = "873--877",
journal = "Heterocycles",
issn = "0385-5414",
publisher = "Japan Institute of Heterocyclic Chemistry",
number = "2",

}

TY - JOUR

T1 - Synthesis of zanthoxyline and its related compounds

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

UR - http://www.scopus.com/inward/record.url?scp=77955671552&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=77955671552&partnerID=8YFLogxK

U2 - 10.3987/COM-09-S(S)111

DO - 10.3987/COM-09-S(S)111

M3 - Article

VL - 80

SP - 873

EP - 877

JO - Heterocycles

JF - Heterocycles

SN - 0385-5414

IS - 2

ER -