β-selective C-H arylation of pyrroles leading to concise syntheses of lamellarins C and I

Kirika Ueda, Kazuma Amaike, Richard M. Maceiczyk, Kenichiro Itami, Junichiro Yamaguchi

Research output: Contribution to journalArticle

75 Citations (Scopus)

Abstract

The first general β-selective C-H arylation of pyrroles has been developed by using a rhodium catalyst. This C-H arylation reaction, which is retrosynthetically straightforward but results in unusual regioselectivity, could result in de novo syntheses of pyrrole-derived natural products and pharmaceuticals. As such, we have successfully synthesized polycyclic marine pyrrole alkaloids, lamellarins C and I, by using this β-selective arylation of pyrroles with aryl iodides (C-H/C-I coupling) and a new double C-H/C-H coupling as key steps.

Original languageEnglish
Pages (from-to)13226-13232
Number of pages7
JournalJournal of the American Chemical Society
Volume136
Issue number38
DOIs
Publication statusPublished - 2014 Sep 24
Externally publishedYes

Fingerprint

Regioselectivity
Alkaloids
Pyrroles
Rhodium
Drug products
Catalysts
Iodides
Biological Products
lamellarin I
lamellarin C
Pharmaceutical Preparations

ASJC Scopus subject areas

  • Chemistry(all)
  • Catalysis
  • Biochemistry
  • Colloid and Surface Chemistry
  • Medicine(all)

Cite this

β-selective C-H arylation of pyrroles leading to concise syntheses of lamellarins C and I. / Ueda, Kirika; Amaike, Kazuma; Maceiczyk, Richard M.; Itami, Kenichiro; Yamaguchi, Junichiro.

In: Journal of the American Chemical Society, Vol. 136, No. 38, 24.09.2014, p. 13226-13232.

Research output: Contribution to journalArticle

Ueda, Kirika ; Amaike, Kazuma ; Maceiczyk, Richard M. ; Itami, Kenichiro ; Yamaguchi, Junichiro. / β-selective C-H arylation of pyrroles leading to concise syntheses of lamellarins C and I. In: Journal of the American Chemical Society. 2014 ; Vol. 136, No. 38. pp. 13226-13232.
@article{69a59269f53f4b3da52943b0eff1cfa4,
title = "β-selective C-H arylation of pyrroles leading to concise syntheses of lamellarins C and I",
abstract = "The first general β-selective C-H arylation of pyrroles has been developed by using a rhodium catalyst. This C-H arylation reaction, which is retrosynthetically straightforward but results in unusual regioselectivity, could result in de novo syntheses of pyrrole-derived natural products and pharmaceuticals. As such, we have successfully synthesized polycyclic marine pyrrole alkaloids, lamellarins C and I, by using this β-selective arylation of pyrroles with aryl iodides (C-H/C-I coupling) and a new double C-H/C-H coupling as key steps.",
author = "Kirika Ueda and Kazuma Amaike and Maceiczyk, {Richard M.} and Kenichiro Itami and Junichiro Yamaguchi",
year = "2014",
month = "9",
day = "24",
doi = "10.1021/ja508449y",
language = "English",
volume = "136",
pages = "13226--13232",
journal = "Journal of the American Chemical Society",
issn = "0002-7863",
publisher = "American Chemical Society",
number = "38",

}

TY - JOUR

T1 - β-selective C-H arylation of pyrroles leading to concise syntheses of lamellarins C and I

AU - Ueda, Kirika

AU - Amaike, Kazuma

AU - Maceiczyk, Richard M.

AU - Itami, Kenichiro

AU - Yamaguchi, Junichiro

PY - 2014/9/24

Y1 - 2014/9/24

N2 - The first general β-selective C-H arylation of pyrroles has been developed by using a rhodium catalyst. This C-H arylation reaction, which is retrosynthetically straightforward but results in unusual regioselectivity, could result in de novo syntheses of pyrrole-derived natural products and pharmaceuticals. As such, we have successfully synthesized polycyclic marine pyrrole alkaloids, lamellarins C and I, by using this β-selective arylation of pyrroles with aryl iodides (C-H/C-I coupling) and a new double C-H/C-H coupling as key steps.

AB - The first general β-selective C-H arylation of pyrroles has been developed by using a rhodium catalyst. This C-H arylation reaction, which is retrosynthetically straightforward but results in unusual regioselectivity, could result in de novo syntheses of pyrrole-derived natural products and pharmaceuticals. As such, we have successfully synthesized polycyclic marine pyrrole alkaloids, lamellarins C and I, by using this β-selective arylation of pyrroles with aryl iodides (C-H/C-I coupling) and a new double C-H/C-H coupling as key steps.

UR - http://www.scopus.com/inward/record.url?scp=84919891502&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84919891502&partnerID=8YFLogxK

U2 - 10.1021/ja508449y

DO - 10.1021/ja508449y

M3 - Article

C2 - 25190257

AN - SCOPUS:84919891502

VL - 136

SP - 13226

EP - 13232

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

SN - 0002-7863

IS - 38

ER -