Stereochemistry of enacyloxins. Part 3. (12′S,17′R,18′S,19′R)-Absolute configuration of enacyloxins, a series of antibiotics from frateuria sp. W-315

R. Takeuchi, Hiromasa Kiyota, M. Yaosaka, T. Watanabe, K. Enari, T. Sugiyama, T. Oritani

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Abstract

The absolute configuration of the 12′,17′,18′,19′-positions of enacyloxins (ENXs), a series of polyhydroxy-polyenic antibiotics from Frateuria sp. W-315, was determined. As degradation of decarbamoyl (dec) ENX IIa gave (5R,6S,1′E)-6-(but-1′-enyl)-5-chloro-5,6-dihydro-2H-pyran-2-one, which corresponded to the 15′-23′ skeleton of dec ENX IIa, its enantiomers were synthesized from tri-O-acetyl-3-glucal. Comparison of the HPLC retention time of these naturally derived and synthetic compounds revealed the 17′R,18′S,19′R-configuration of ENXs. Hydrogenation and oxidation of ENX IIa gave methyl 13-hydroxy-6,12-dimethyltridecanoate, which was converted to the 13-MTPA ester. Comparison of the 1H NMR chemical shifts and the coupling constants with the model compounds revealed the 12′S-configuration. This absolute stereochemistry is necessarily applicable to other enacyloxins.

Original languageEnglish
Pages (from-to)2676-2681
Number of pages6
JournalJournal of the Chemical Society, Perkin Transactions 1
Issue number20
Publication statusPublished - 2001
Externally publishedYes

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ASJC Scopus subject areas

  • Chemistry(all)

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