Total synthesis of benzo[c]phenanthridine alkaloids, chelerythrine and 12-methoxydihydrochelerythrine, by a palladium-assisted internal biaryl coupling reaction

T. Harayama; T. Akiyama; H. Akamatsu; K. Kawano; H. Abe; Y. Takeuchi

doi:10.1055/s-2001-11424

Total synthesis of benzo[c]phenanthridine alkaloids, chelerythrine and 12-methoxydihydrochelerythrine, by a palladium-assisted internal biaryl coupling reaction

T. Harayama, T. Akiyama, H. Akamatsu, K. Kawano, H. Abe, Y. Takeuchi

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

71 Citations (Scopus)

Abstract

A covenient and versatile synthesis of benzo[c]phenanthridine alkaloids, chelerythrine (1) and 12-methoxydihydrochelerythrine (5), was accomplished via an internal aryl-aryl coupling reaction of haloamides 8 and 9 by a palladium-assisted cyclization reaction.

Original language	English
Pages (from-to)	444-450
Number of pages	7
Journal	Synthesis
Issue number	3
DOIs	https://doi.org/10.1055/s-2001-11424
Publication status	Published - 2001

Keywords

Alkaloids
Haloamides
Heck-type reaction
Internal aryl-aryl coupling
Palladium
Ring closure

ASJC Scopus subject areas

Catalysis
Organic Chemistry

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abstract = "A covenient and versatile synthesis of benzo[c]phenanthridine alkaloids, chelerythrine (1) and 12-methoxydihydrochelerythrine (5), was accomplished via an internal aryl-aryl coupling reaction of haloamides 8 and 9 by a palladium-assisted cyclization reaction.",

keywords = "Alkaloids, Haloamides, Heck-type reaction, Internal aryl-aryl coupling, Palladium, Ring closure",

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year = "2001",

doi = "10.1055/s-2001-11424",

language = "English",

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AU - Harayama, T.

AU - Akiyama, T.

AU - Akamatsu, H.

AU - Kawano, K.

AU - Abe, H.

AU - Takeuchi, Y.

PY - 2001

Y1 - 2001

N2 - A covenient and versatile synthesis of benzo[c]phenanthridine alkaloids, chelerythrine (1) and 12-methoxydihydrochelerythrine (5), was accomplished via an internal aryl-aryl coupling reaction of haloamides 8 and 9 by a palladium-assisted cyclization reaction.

AB - A covenient and versatile synthesis of benzo[c]phenanthridine alkaloids, chelerythrine (1) and 12-methoxydihydrochelerythrine (5), was accomplished via an internal aryl-aryl coupling reaction of haloamides 8 and 9 by a palladium-assisted cyclization reaction.

KW - Alkaloids

KW - Haloamides

KW - Heck-type reaction

KW - Internal aryl-aryl coupling

KW - Palladium

KW - Ring closure

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Total synthesis of benzo[c]phenanthridine alkaloids, chelerythrine and 12-methoxydihydrochelerythrine, by a palladium-assisted internal biaryl coupling reaction

Abstract

Keywords

ASJC Scopus subject areas

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