Unified Approach toward Syntheses of Juglomycins and Their Derivatives

Kai Yoshioka; Shogo Kamo; Keisuke Hosaka; Ryohei Sato; Yuma Miikeda; Yuri Manabe; Shusuke Tomoshige; Kazunori Tsubaki; Kouji Kuramochi

doi:10.1021/acsomega.9b01376

Unified Approach toward Syntheses of Juglomycins and Their Derivatives

Kai Yoshioka, Shogo Kamo, Keisuke Hosaka, Ryohei Sato, Yuma Miikeda, Yuri Manabe, Shusuke Tomoshige, Kazunori Tsubaki, Kouji Kuramochi

生命科学研究科・分子化学生物学専攻

研究成果: Article › 査読

抄録

A unified and common intermediate strategy for syntheses of juglomycins and their derivatives is reported. The use of a 1,4-dimethoxynaphthalene derivative as a key intermediate enabled easy access to various juglomycin derivatives. In this study, juglomycins A-D, juglomycin C amide, khatmiamycin and its 4-epimer, and the structure proposed for juglomycin Z were synthesized from this intermediate. The absolute configuration of natural khatmiamycin has been established to be 3R,4R through our synthesis. Unfortunately, the spectroscopic data for synthetic juglomycin Z were not consistent with the data reported for the natural one, strongly suggesting a structural misassignment.

本文言語	English
ページ（範囲）	11737-11748
ページ数	12
ジャーナル	ACS Omega
巻	4
号	7
DOI	https://doi.org/10.1021/acsomega.9b01376
出版ステータス	Published - 2019 7 31

ASJC Scopus subject areas

Chemistry(all)
Chemical Engineering(all)

文献へのアクセス

10.1021/acsomega.9b01376

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引用スタイル

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abstract = "A unified and common intermediate strategy for syntheses of juglomycins and their derivatives is reported. The use of a 1,4-dimethoxynaphthalene derivative as a key intermediate enabled easy access to various juglomycin derivatives. In this study, juglomycins A-D, juglomycin C amide, khatmiamycin and its 4-epimer, and the structure proposed for juglomycin Z were synthesized from this intermediate. The absolute configuration of natural khatmiamycin has been established to be 3R,4R through our synthesis. Unfortunately, the spectroscopic data for synthetic juglomycin Z were not consistent with the data reported for the natural one, strongly suggesting a structural misassignment.",

author = "Kai Yoshioka and Shogo Kamo and Keisuke Hosaka and Ryohei Sato and Yuma Miikeda and Yuri Manabe and Shusuke Tomoshige and Kazunori Tsubaki and Kouji Kuramochi",

note = "Funding Information: This study was partly supported by a Grant-in Aid from the Japan Society for the Promotion of Science (JSPS) Fellows (no. 16J00542) to S.K. and a Grant-in-Aid for Scientific Research (C) (KAKENHI no. 15K07416) and the Sumitomo Foundation (no. 170183) to K.K.",

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AU - Yoshioka, Kai

AU - Kamo, Shogo

AU - Hosaka, Keisuke

AU - Sato, Ryohei

AU - Miikeda, Yuma

AU - Manabe, Yuri

AU - Tomoshige, Shusuke

AU - Tsubaki, Kazunori

AU - Kuramochi, Kouji

N1 - Funding Information: This study was partly supported by a Grant-in Aid from the Japan Society for the Promotion of Science (JSPS) Fellows (no. 16J00542) to S.K. and a Grant-in-Aid for Scientific Research (C) (KAKENHI no. 15K07416) and the Sumitomo Foundation (no. 170183) to K.K.

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