4.5 Article

Assignment of Absolute Configuration of Bis-γ-pyrone Polypropionates from Marine Pulmonate Molluscs

Journal

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2012, Issue 6, Pages 1107-1111

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201101587

Keywords

Natural products; Configuration determination; Polyketides; Circular dichroism

Funding

  1. National Marine 863 Project [2011AA09070102]
  2. National Natural Science Foundation of China [21021063, 21072204]
  3. Science and Technology Commission of Shanghai Municipality (STCSM) [10540702900]
  4. State Key Laboratory of Drug Research/Shanghai Institute of Materia Medica (SKLDR/SIMM) [SIMM1105 KF-04, SIMM1106 KF-11]
  5. Hungarian-Chinese Intergovernmental S&T Cooperation Programme
  6. Chinese Academy of Sciences (CAS) [KSCX2-YW-R-18]
  7. Hungarian Scientific Research Fund (OTKA) [K-81701, TAMOP 4.2.1./B-09/1/KONV-2010-0007]

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The absolute configurations of onchidione (1), previously reported from the marine pulmonate Onchidium sp., and the related alcohols onchidiol (2) and 4-epi-onchidiol (3), first described as methanolysis products of 1, were assigned by X-ray diffraction analysis and solid-state time-dependent density functional theory electronic circular dichroism. Alcohol 3 was incorrectly reported as the C-16 epimer of 2.

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