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

doi:10.1021/ja508449y

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

^*Corresponding author for this work

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

111 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 language	English
Pages (from-to)	13226-13232
Number of pages	7
Journal	Journal of the American Chemical Society
Volume	136
Issue number	38
DOIs	https://doi.org/10.1021/ja508449y
Publication status	Published - 2014 Sept 24
Externally published	Yes

ASJC Scopus subject areas

Catalysis
Chemistry(all)
Biochemistry
Colloid and Surface Chemistry

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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.",

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AU - Ueda, Kirika

AU - Amaike, Kazuma

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AU - Itami, Kenichiro

AU - Yamaguchi, Junichiro

PY - 2014/9/24

Y1 - 2014/9/24

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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.

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

Abstract

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