Total synthesis of calothrixins A and B by palladium-catalyzed tandem cyclization/cross-coupling reaction of indolylborate

Takumi Abe; Toshiaki Ikeda; Tominari Choshi; Satoshi Hibino; Noriyuki Hatae; Eiko Toyata; Reiko Yanada; Minoru Ishikura

doi:10.1002/ejoc.201200657

Total synthesis of calothrixins A and B by palladium-catalyzed tandem cyclization/cross-coupling reaction of indolylborate

Takumi Abe, Toshiaki Ikeda, Tominari Choshi, Satoshi Hibino, Noriyuki Hatae, Eiko Toyata, Reiko Yanada, Minoru Ishikura

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

45 Citations (Scopus)

Abstract

The palladium-catalyzed tandem cyclization/cross-coupling reaction of triethyl(indol-2-yl)borate with vinyl bromide was successfully used in the concise total synthesis of the indolophenanthridine alkaloids, calothrixins A and B. Palladium-catalyzed cross-coupling reaction of indolylborate with vinyl bromide proceeded smoothly, leading to triene. This intermediate was successfully used for the total synthesis of calothrixins A and B.

Original language	English
Pages (from-to)	5018-5027
Number of pages	10
Journal	European Journal of Organic Chemistry
Issue number	26
DOIs	https://doi.org/10.1002/ejoc.201200657
Publication status	Published - Sept 2012
Externally published	Yes

Keywords

Copper
Cross-coupling
Electrocyclic reactions
Palladium
Total synthesis

ASJC Scopus subject areas

Physical and Theoretical Chemistry
Organic Chemistry

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10.1002/ejoc.201200657

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title = "Total synthesis of calothrixins A and B by palladium-catalyzed tandem cyclization/cross-coupling reaction of indolylborate",

abstract = "The palladium-catalyzed tandem cyclization/cross-coupling reaction of triethyl(indol-2-yl)borate with vinyl bromide was successfully used in the concise total synthesis of the indolophenanthridine alkaloids, calothrixins A and B. Palladium-catalyzed cross-coupling reaction of indolylborate with vinyl bromide proceeded smoothly, leading to triene. This intermediate was successfully used for the total synthesis of calothrixins A and B.",

keywords = "Copper, Cross-coupling, Electrocyclic reactions, Palladium, Total synthesis",

author = "Takumi Abe and Toshiaki Ikeda and Tominari Choshi and Satoshi Hibino and Noriyuki Hatae and Eiko Toyata and Reiko Yanada and Minoru Ishikura",

year = "2012",

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doi = "10.1002/ejoc.201200657",

language = "English",

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T1 - Total synthesis of calothrixins A and B by palladium-catalyzed tandem cyclization/cross-coupling reaction of indolylborate

AU - Abe, Takumi

AU - Ikeda, Toshiaki

AU - Choshi, Tominari

AU - Hibino, Satoshi

AU - Hatae, Noriyuki

AU - Toyata, Eiko

AU - Yanada, Reiko

AU - Ishikura, Minoru

PY - 2012/9

Y1 - 2012/9

N2 - The palladium-catalyzed tandem cyclization/cross-coupling reaction of triethyl(indol-2-yl)borate with vinyl bromide was successfully used in the concise total synthesis of the indolophenanthridine alkaloids, calothrixins A and B. Palladium-catalyzed cross-coupling reaction of indolylborate with vinyl bromide proceeded smoothly, leading to triene. This intermediate was successfully used for the total synthesis of calothrixins A and B.

AB - The palladium-catalyzed tandem cyclization/cross-coupling reaction of triethyl(indol-2-yl)borate with vinyl bromide was successfully used in the concise total synthesis of the indolophenanthridine alkaloids, calothrixins A and B. Palladium-catalyzed cross-coupling reaction of indolylborate with vinyl bromide proceeded smoothly, leading to triene. This intermediate was successfully used for the total synthesis of calothrixins A and B.

KW - Copper

KW - Cross-coupling

KW - Electrocyclic reactions

KW - Palladium

KW - Total synthesis

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JO - Justus Liebigs Annalen der Chemie

JF - Justus Liebigs Annalen der Chemie

IS - 26

ER -

Total synthesis of calothrixins A and B by palladium-catalyzed tandem cyclization/cross-coupling reaction of indolylborate

Abstract

Keywords

ASJC Scopus subject areas

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