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

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12 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 languageEnglish
Pages (from-to)114-132
Number of pages19
JournalJournal of Organic Chemistry
Volume80
Issue number1
DOIs
Publication statusPublished - 2015

ASJC Scopus subject areas

  • Organic Chemistry

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