Protecting-group-free total synthesis of (-)-rhazinilam and (-)-rhazinicine using a gold-catalyzed cascade cyclization

Kenji Sugimoto; Kazuki Toyoshima; Shiori Nonaka; Kenta Kotaki; Hirofumi Ueda; Hidetoshi Tokuyama

doi:10.1002/anie.201303067

Protecting-group-free total synthesis of (-)-rhazinilam and (-)-rhazinicine using a gold-catalyzed cascade cyclization

Kenji Sugimoto, Kazuki Toyoshima, Shiori Nonaka, Kenta Kotaki, Hirofumi Ueda, Hidetoshi Tokuyama

薬品製造学研究室

研究成果: ジャーナルへの寄稿 › 学術論文 › 査読

95 被引用数 (Scopus)

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'Rhaz'zmatazz: A total synthesis of (-)-rhazinilam and the first asymmetric total synthesis of (-)-rhazinicine were accomplished by using constructing the indolizinone core through the gold-catalyzed cyclization of a fully elaborated linear ynamide. The scope and generality of this cascade reaction for the construction of highly substituted indolizinones were also investigated.

本文言語	英語
ページ（範囲）	7168-7171
ページ数	4
ジャーナル	Angewandte Chemie - International Edition
巻	52
号	28
DOI	https://doi.org/10.1002/anie.201303067
出版ステータス	出版済み - 2013/07/08

ASJC Scopus 主題領域

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化学一般

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10.1002/anie.201303067

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title = "Protecting-group-free total synthesis of (-)-rhazinilam and (-)-rhazinicine using a gold-catalyzed cascade cyclization",

abstract = "'Rhaz'zmatazz: A total synthesis of (-)-rhazinilam and the first asymmetric total synthesis of (-)-rhazinicine were accomplished by using constructing the indolizinone core through the gold-catalyzed cyclization of a fully elaborated linear ynamide. The scope and generality of this cascade reaction for the construction of highly substituted indolizinones were also investigated.",

keywords = "alkaloids, cyclization, gold, natural products, total synthesis",

author = "Kenji Sugimoto and Kazuki Toyoshima and Shiori Nonaka and Kenta Kotaki and Hirofumi Ueda and Hidetoshi Tokuyama",

year = "2013",

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T1 - Protecting-group-free total synthesis of (-)-rhazinilam and (-)-rhazinicine using a gold-catalyzed cascade cyclization

AU - Sugimoto, Kenji

AU - Toyoshima, Kazuki

AU - Nonaka, Shiori

AU - Kotaki, Kenta

AU - Ueda, Hirofumi

AU - Tokuyama, Hidetoshi

PY - 2013/7/8

Y1 - 2013/7/8

N2 - 'Rhaz'zmatazz: A total synthesis of (-)-rhazinilam and the first asymmetric total synthesis of (-)-rhazinicine were accomplished by using constructing the indolizinone core through the gold-catalyzed cyclization of a fully elaborated linear ynamide. The scope and generality of this cascade reaction for the construction of highly substituted indolizinones were also investigated.

AB - 'Rhaz'zmatazz: A total synthesis of (-)-rhazinilam and the first asymmetric total synthesis of (-)-rhazinicine were accomplished by using constructing the indolizinone core through the gold-catalyzed cyclization of a fully elaborated linear ynamide. The scope and generality of this cascade reaction for the construction of highly substituted indolizinones were also investigated.

KW - alkaloids

KW - cyclization

KW - gold

KW - natural products

KW - total synthesis

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DO - 10.1002/anie.201303067

M3 - 学術論文

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JF - Angewandte Chemie - International Edition

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Protecting-group-free total synthesis of (-)-rhazinilam and (-)-rhazinicine using a gold-catalyzed cascade cyclization

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