An approach for the synthesis of nakamuric acid

Xiaolei Wang; Chuo Chen

doi:10.1016/j.tet.2014.10.027

An approach for the synthesis of nakamuric acid

Xiaolei Wang, Chuo Chen

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

16 Scopus citations

Abstract

The biosynthesis of dimeric pyrrole-imidazole alkaloids is likely mediated by enzyme-catalyzed reversible single-electron transfer (SET) cycloaddition. We now show that Ir(ppy)₃ can promote SET-mediated formal [2+2] and [4+2] cycloaddition reactions of pyrrole-imidazole alkaloids-related substrates under photolytic conditions. This biomimetic approach is useful for the construction of the core skeleton of nakamuric acid and sceptrin.

Original language	English (US)
Pages (from-to)	3690-3693
Number of pages	4
Journal	Tetrahedron
Volume	71
Issue number	22
DOIs	https://doi.org/10.1016/j.tet.2014.10.027
State	Published - Jun 3 2015

Keywords

Cyclization
Imidazole
Pyrrole
Radical
Single-electron transfer

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tet.2014.10.027

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title = "An approach for the synthesis of nakamuric acid",

abstract = "The biosynthesis of dimeric pyrrole-imidazole alkaloids is likely mediated by enzyme-catalyzed reversible single-electron transfer (SET) cycloaddition. We now show that Ir(ppy)3 can promote SET-mediated formal [2+2] and [4+2] cycloaddition reactions of pyrrole-imidazole alkaloids-related substrates under photolytic conditions. This biomimetic approach is useful for the construction of the core skeleton of nakamuric acid and sceptrin.",

keywords = "Cyclization, Imidazole, Pyrrole, Radical, Single-electron transfer",

author = "Xiaolei Wang and Chuo Chen",

note = "Funding Information: Financial Support was provided by the NIH (NIGMS R01-GM079554 ), the Welch Foundation ( I-1596 ), and UT Southwestern . C.C. is a Southwestern Medical Foundation Scholar in Biomedical Research. Publisher Copyright: {\textcopyright} 2014 Elsevier Ltd. All rights reserved.",

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AU - Wang, Xiaolei

AU - Chen, Chuo

N1 - Funding Information: Financial Support was provided by the NIH (NIGMS R01-GM079554 ), the Welch Foundation ( I-1596 ), and UT Southwestern . C.C. is a Southwestern Medical Foundation Scholar in Biomedical Research. Publisher Copyright: © 2014 Elsevier Ltd. All rights reserved.

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N2 - The biosynthesis of dimeric pyrrole-imidazole alkaloids is likely mediated by enzyme-catalyzed reversible single-electron transfer (SET) cycloaddition. We now show that Ir(ppy)3 can promote SET-mediated formal [2+2] and [4+2] cycloaddition reactions of pyrrole-imidazole alkaloids-related substrates under photolytic conditions. This biomimetic approach is useful for the construction of the core skeleton of nakamuric acid and sceptrin.

AB - The biosynthesis of dimeric pyrrole-imidazole alkaloids is likely mediated by enzyme-catalyzed reversible single-electron transfer (SET) cycloaddition. We now show that Ir(ppy)3 can promote SET-mediated formal [2+2] and [4+2] cycloaddition reactions of pyrrole-imidazole alkaloids-related substrates under photolytic conditions. This biomimetic approach is useful for the construction of the core skeleton of nakamuric acid and sceptrin.

KW - Cyclization

KW - Imidazole

KW - Pyrrole

KW - Radical

KW - Single-electron transfer

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JF - Tetrahedron

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An approach for the synthesis of nakamuric acid

Abstract

Keywords

ASJC Scopus subject areas

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