Total synthesis and structure determination of JBIR-108 - A 2-hydroxy-2-(1-hydroxyethyl)-2,3-dihydro-3(2H)-furanone Isolated from Streptomyces gramineus IR087Pi-4

Koichi Fujiwara; Hirokazu Tsukamoto; Miho Izumikawa; Takahiro Hosoya; Noritaka Kagaya; Motoki Takagi; Hideki Yamamura; Masayuki Hayakawa; Kazuo Shin-Ya; Takayuki Doi

doi:10.1021/jo502198y

Total synthesis and structure determination of JBIR-108 - A 2-hydroxy-2-(1-hydroxyethyl)-2,3-dihydro-3(2H)-furanone Isolated from Streptomyces gramineus IR087Pi-4

Koichi Fujiwara, Hirokazu Tsukamoto, Miho Izumikawa, Takahiro Hosoya, Noritaka Kagaya, Motoki Takagi, Hideki Yamamura, Masayuki Hayakawa, Kazuo Shin-Ya, Takayuki Doi

PHA - Molecular Pharmaceutical Science

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

15 Citations (Scopus)

Abstract

The planar and stereostructures of JBIR-108 isolated from Streptomyces gramineus IR087Pi-4 were determined partly by spectral analysis, and these structural assignments were confirmed and completed by the total synthesis of both 1-epimers. The key stereocenters in JBIR-108 were constructed via a Corey-Bakshi-Shibata (CBS) reduction (C-1), vinylogous Mukaiyama aldol reaction (C-7), and Brown crotylation (C-14 and C-15). Although it was difficult to determine the stereochemistries at the C-1 and C-7 positions in the natural product using the modified Mosher's method, the synthesis of two possible C-1 diastereomers enabled the identification of the configurations at the hitherto unknown stereocenters.

Original language	English
Pages (from-to)	114-132
Number of pages	19
Journal	Journal of Organic Chemistry
Volume	80
Issue number	1
DOIs	https://doi.org/10.1021/jo502198y
Publication status	Published - 2015 Jan 2

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Fujiwara, K., Tsukamoto, H., Izumikawa, M., Hosoya, T., Kagaya, N., Takagi, M., Yamamura, H., Hayakawa, M., Shin-Ya, K., & Doi, T. (2015). Total synthesis and structure determination of JBIR-108 - A 2-hydroxy-2-(1-hydroxyethyl)-2,3-dihydro-3(2H)-furanone Isolated from Streptomyces gramineus IR087Pi-4. Journal of Organic Chemistry, 80(1), 114-132. https://doi.org/10.1021/jo502198y

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title = "Total synthesis and structure determination of JBIR-108 - A 2-hydroxy-2-(1-hydroxyethyl)-2,3-dihydro-3(2H)-furanone Isolated from Streptomyces gramineus IR087Pi-4",

abstract = "The planar and stereostructures of JBIR-108 isolated from Streptomyces gramineus IR087Pi-4 were determined partly by spectral analysis, and these structural assignments were confirmed and completed by the total synthesis of both 1-epimers. The key stereocenters in JBIR-108 were constructed via a Corey-Bakshi-Shibata (CBS) reduction (C-1), vinylogous Mukaiyama aldol reaction (C-7), and Brown crotylation (C-14 and C-15). Although it was difficult to determine the stereochemistries at the C-1 and C-7 positions in the natural product using the modified Mosher's method, the synthesis of two possible C-1 diastereomers enabled the identification of the configurations at the hitherto unknown stereocenters.",

author = "Koichi Fujiwara and Hirokazu Tsukamoto and Miho Izumikawa and Takahiro Hosoya and Noritaka Kagaya and Motoki Takagi and Hideki Yamamura and Masayuki Hayakawa and Kazuo Shin-Ya and Takayuki Doi",

note = "Funding Information: This work was supported by a grant from the New Energy and Industrial Technology Department Organization (NEDO) of Japan and a Grant-in-Aid for Scientific Research (23380067 to K.S.-y.) from the Japan Society for the Promotion of Science (JSPS). Publisher Copyright: {\textcopyright} 2014 American Chemical Society.",

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doi = "10.1021/jo502198y",

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Fujiwara, K, Tsukamoto, H, Izumikawa, M, Hosoya, T, Kagaya, N, Takagi, M, Yamamura, H, Hayakawa, M, Shin-Ya, K & Doi, T 2015, 'Total synthesis and structure determination of JBIR-108 - A 2-hydroxy-2-(1-hydroxyethyl)-2,3-dihydro-3(2H)-furanone Isolated from Streptomyces gramineus IR087Pi-4', Journal of Organic Chemistry, vol. 80, no. 1, pp. 114-132. https://doi.org/10.1021/jo502198y

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AU - Fujiwara, Koichi

AU - Tsukamoto, Hirokazu

AU - Izumikawa, Miho

AU - Hosoya, Takahiro

AU - Kagaya, Noritaka

AU - Takagi, Motoki

AU - Yamamura, Hideki

AU - Hayakawa, Masayuki

AU - Shin-Ya, Kazuo

AU - Doi, Takayuki

N1 - Funding Information: This work was supported by a grant from the New Energy and Industrial Technology Department Organization (NEDO) of Japan and a Grant-in-Aid for Scientific Research (23380067 to K.S.-y.) from the Japan Society for the Promotion of Science (JSPS). Publisher Copyright: © 2014 American Chemical Society.

PY - 2015/1/2

Y1 - 2015/1/2

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AB - The planar and stereostructures of JBIR-108 isolated from Streptomyces gramineus IR087Pi-4 were determined partly by spectral analysis, and these structural assignments were confirmed and completed by the total synthesis of both 1-epimers. The key stereocenters in JBIR-108 were constructed via a Corey-Bakshi-Shibata (CBS) reduction (C-1), vinylogous Mukaiyama aldol reaction (C-7), and Brown crotylation (C-14 and C-15). Although it was difficult to determine the stereochemistries at the C-1 and C-7 positions in the natural product using the modified Mosher's method, the synthesis of two possible C-1 diastereomers enabled the identification of the configurations at the hitherto unknown stereocenters.

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Total synthesis and structure determination of JBIR-108 - A 2-hydroxy-2-(1-hydroxyethyl)-2,3-dihydro-3(2H)-furanone Isolated from Streptomyces gramineus IR087Pi-4

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