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

72 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

Access to Document

10.1055/s-2001-11424

Cite this

@article{5ab4b93e4276442690d9b57167c6a98d,

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

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",

author = "T. Harayama and T. Akiyama and H. Akamatsu and K. Kawano and H. Abe and Y. Takeuchi",

year = "2001",

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

language = "English",

pages = "444--450",

journal = "Synthesis",

issn = "0039-7881",

publisher = "Georg Thieme Verlag",

number = "3",

}

TY - JOUR

T1 - Total synthesis of benzo[c]phenanthridine alkaloids, chelerythrine and 12-methoxydihydrochelerythrine, by a palladium-assisted internal biaryl coupling reaction

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

UR - http://www.scopus.com/inward/record.url?scp=0035108645&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0035108645&partnerID=8YFLogxK

U2 - 10.1055/s-2001-11424

DO - 10.1055/s-2001-11424

M3 - Article

AN - SCOPUS:0035108645

SP - 444

EP - 450

JO - Synthesis

JF - Synthesis

SN - 0039-7881

IS - 3

ER -

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

Access to Document

Other files and links

Fingerprint

Cite this