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.
authors.affiliation: †Graduate School of Pharmaceutical Sciences, Tohoku University, 6-3 Aza-aoba, Aramaki, Aoba-ku, Sendai 980-8578, Japan.
authors.forename: Koichi
authors.initials: K
authors.lastname: Fujiwara
authors.affiliation: †Graduate School of Pharmaceutical Sciences, Tohoku University, 6-3 Aza-aoba, Aramaki, Aoba-ku, Sendai 980-8578, Japan.
authors.forename: Hirokazu
authors.initials: H
authors.lastname: Tsukamoto
authors.affiliation: ‡Japan Biological Informatics Consortium (JBIC), 2-4-7 Aomi, Koto-ku, Tokyo 135-0064, Japan.
authors.forename: Miho
authors.initials: M
authors.lastname: Izumikawa
authors.affiliation: ‡Japan Biological Informatics Consortium (JBIC), 2-4-7 Aomi, Koto-ku, Tokyo 135-0064, Japan.
authors.forename: Takahiro
authors.initials: T
authors.lastname: Hosoya
authors.affiliation: §National Institute of Advanced Industrial Science and Technology (AIST), 2-4-7 Aomi, Koto-ku, Tokyo 135-0064, Japan.
authors.forename: Noritaka
authors.initials: N
authors.lastname: Kagaya
authors.affiliation: ‡Japan Biological Informatics Consortium (JBIC), 2-4-7 Aomi, Koto-ku, Tokyo 135-0064, Japan.
authors.forename: Motoki
authors.initials: M
authors.lastname: Takagi
authors.affiliation: ∥Interdisciplinary Graduate School of Medicine and Engineering, University of Yamanashi, Takeda-4, Kofu 400-8511, Japan.
authors.forename: Hideki
authors.initials: H
authors.lastname: Yamamura
authors.affiliation: ∥Interdisciplinary Graduate School of Medicine and Engineering, University of Yamanashi, Takeda-4, Kofu 400-8511, Japan.
authors.forename: Masayuki
authors.initials: M
authors.lastname: Hayakawa
authors.affiliation: §National Institute of Advanced Industrial Science and Technology (AIST), 2-4-7 Aomi, Koto-ku, Tokyo 135-0064, Japan.
authors.forename: Kazuo
authors.initials: K
authors.lastname: Shin-Ya
authors.affiliation: †Graduate School of Pharmaceutical Sciences, Tohoku University, 6-3 Aza-aoba, Aramaki, Aoba-ku, Sendai 980-8578, Japan.
authors.forename: Takayuki
authors.initials: T
authors.lastname: Doi
mesh_terms: D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry / Q000302:isolation & purification*; D008968:Molecular Conformation; D015394:Molecular Structure; D013302:Streptomyces / Q000737:chemistry*
chemical_list: D005663:Furans; C000599559:JBIR-108-A