Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 16, Issue 23, Pages 6933-6941Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201000189
Keywords
asymmetric synthesis; chirality; natural products; plakortone B; structure elucidation
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Funding
- University Grants Committee of the Hong Kong SAR, China [AoE/9-10/01]
- Chinese University of Hong Kong
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Plakortone B is a naturally occurring bicyclic[3.3.0]furanolactone compound with attractive bioactivities. Although the relative configuration of plakortone B's central core had been established by NMR spectroscopic methods, the absolute configuration of its four stereocenters remained unknown. In the present paper, all four possible isomers of plakortone B were synthesized and one of these molecules was round to be identical with the natural plakortone B on the basis of H-1. C-13 NMR spectra and specific rotation comparisons. Thus, the absolute configuration of the natural plakortone B was determined to be (3S.4S,6R.10R).
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