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

PHA - Molecular Pharmaceutical Science

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

72 Citations (Scopus)

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.

Original language	English
Pages (from-to)	7168-7171
Number of pages	4
Journal	Angewandte Chemie - International Edition
Volume	52
Issue number	28
DOIs	https://doi.org/10.1002/anie.201303067
Publication status	Published - 2013 Jul 8

Keywords

alkaloids
cyclization
gold
natural products
total synthesis

ASJC Scopus subject areas

Catalysis
Chemistry(all)

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10.1002/anie.201303067

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Protecting-group-free total synthesis of (-)-rhazinilam and (-)-rhazinicine using a gold-catalyzed cascade cyclization. / Sugimoto, Kenji; Toyoshima, Kazuki; Nonaka, Shiori; Kotaki, Kenta; Ueda, Hirofumi ; Tokuyama, Hidetoshi.

In: Angewandte Chemie - International Edition, Vol. 52, No. 28, 08.07.2013, p. 7168-7171.

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

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AU - Kotaki, Kenta

AU - Ueda, Hirofumi

AU - Tokuyama, Hidetoshi

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

Abstract

Keywords

ASJC Scopus subject areas

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