Concise Total Syntheses of Pyrido[4,3-b]carbazole Alkaloids Using Copper-Mediated 6π-Electrocyclization

Tomoki Itoh; Takumi Abe; Tominari Choshi; Takashi Nishiyama; Reiko Yanada; Minoru Ishikura

doi:10.1002/ejoc.201600246

Concise Total Syntheses of Pyrido[4,3-b]carbazole Alkaloids Using Copper-Mediated 6π-Electrocyclization

Tomoki Itoh, Takumi Abe, Tominari Choshi, Takashi Nishiyama, Reiko Yanada, Minoru Ishikura

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

19 Citations (Scopus)

Abstract

Concise syntheses of 9-methoxyellipticine, 3,4-dihydroellipticine (μ-alkaloid D), 1,2,3,4-tetrahydroellipticine, 2-methyl-1,2,3,4-tetrahydroellipticine, olivacine, 3,4-dihydroolivacine, (±)-guatambuine, and (±)-janetine were developed starting from hexatriene intermediates readily obtained by Pd-catalyzed tandem cyclization/cross-coupling reaction of indolylborates. The route enables the facile construction of pyrido[4,3-b]carbazoles by Cu-catalyzed 6π-electrocyclization and subsequent transformation of the pyridocarbazole intermediates into pyrido[4,3-b]carbazole alkaloids. Concise total syntheses of pyrido[4,3-b]carbazole alkaloids were accomplished using Cu-catalyzed 6π-electrocyclization of hexatriene as a key step.

Original language	English
Pages (from-to)	2290-2299
Number of pages	10
Journal	European Journal of Organic Chemistry
Volume	2016
Issue number	13
DOIs	https://doi.org/10.1002/ejoc.201600246
Publication status	Published - May 1 2016
Externally published	Yes

Keywords

Alkaloids
Copper
Electrocyclization
Natural products
Nitrogen heterocycles
Total synthesis

ASJC Scopus subject areas

Physical and Theoretical Chemistry
Organic Chemistry

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10.1002/ejoc.201600246

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title = "Concise Total Syntheses of Pyrido[4,3-b]carbazole Alkaloids Using Copper-Mediated 6π-Electrocyclization",

abstract = "Concise syntheses of 9-methoxyellipticine, 3,4-dihydroellipticine (μ-alkaloid D), 1,2,3,4-tetrahydroellipticine, 2-methyl-1,2,3,4-tetrahydroellipticine, olivacine, 3,4-dihydroolivacine, (±)-guatambuine, and (±)-janetine were developed starting from hexatriene intermediates readily obtained by Pd-catalyzed tandem cyclization/cross-coupling reaction of indolylborates. The route enables the facile construction of pyrido[4,3-b]carbazoles by Cu-catalyzed 6π-electrocyclization and subsequent transformation of the pyridocarbazole intermediates into pyrido[4,3-b]carbazole alkaloids. Concise total syntheses of pyrido[4,3-b]carbazole alkaloids were accomplished using Cu-catalyzed 6π-electrocyclization of hexatriene as a key step.",

keywords = "Alkaloids, Copper, Electrocyclization, Natural products, Nitrogen heterocycles, Total synthesis",

author = "Tomoki Itoh and Takumi Abe and Tominari Choshi and Takashi Nishiyama and Reiko Yanada and Minoru Ishikura",

note = "Publisher Copyright: Copyright {\textcopyright} 2016 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.",

year = "2016",

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AU - Itoh, Tomoki

AU - Abe, Takumi

AU - Choshi, Tominari

AU - Nishiyama, Takashi

AU - Yanada, Reiko

AU - Ishikura, Minoru

PY - 2016/5/1

Y1 - 2016/5/1

N2 - Concise syntheses of 9-methoxyellipticine, 3,4-dihydroellipticine (μ-alkaloid D), 1,2,3,4-tetrahydroellipticine, 2-methyl-1,2,3,4-tetrahydroellipticine, olivacine, 3,4-dihydroolivacine, (±)-guatambuine, and (±)-janetine were developed starting from hexatriene intermediates readily obtained by Pd-catalyzed tandem cyclization/cross-coupling reaction of indolylborates. The route enables the facile construction of pyrido[4,3-b]carbazoles by Cu-catalyzed 6π-electrocyclization and subsequent transformation of the pyridocarbazole intermediates into pyrido[4,3-b]carbazole alkaloids. Concise total syntheses of pyrido[4,3-b]carbazole alkaloids were accomplished using Cu-catalyzed 6π-electrocyclization of hexatriene as a key step.

AB - Concise syntheses of 9-methoxyellipticine, 3,4-dihydroellipticine (μ-alkaloid D), 1,2,3,4-tetrahydroellipticine, 2-methyl-1,2,3,4-tetrahydroellipticine, olivacine, 3,4-dihydroolivacine, (±)-guatambuine, and (±)-janetine were developed starting from hexatriene intermediates readily obtained by Pd-catalyzed tandem cyclization/cross-coupling reaction of indolylborates. The route enables the facile construction of pyrido[4,3-b]carbazoles by Cu-catalyzed 6π-electrocyclization and subsequent transformation of the pyridocarbazole intermediates into pyrido[4,3-b]carbazole alkaloids. Concise total syntheses of pyrido[4,3-b]carbazole alkaloids were accomplished using Cu-catalyzed 6π-electrocyclization of hexatriene as a key step.

KW - Alkaloids

KW - Copper

KW - Electrocyclization

KW - Natural products

KW - Nitrogen heterocycles

KW - Total synthesis

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Concise Total Syntheses of Pyrido[4,3-b]carbazole Alkaloids Using Copper-Mediated 6π-Electrocyclization

Abstract

Keywords

ASJC Scopus subject areas

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