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Synthetic Study of Natural Metabolites Containing a Benzo[ c ]oxepine Skeleton: Heterocornol C and D.

Ján GettlerTomáš ČarnýMartin MarkovičPeter KoóšErika SamoľováJán Moncol'Tibor Gracza
Published in: International journal of molecular sciences (2023)
A versatile strategy for the enantioselective synthesis of a benzo[ c ]oxepine structural core containing natural secondary metabolites was developed. The key steps of the synthetic approach include ring-closing alkene metathesis for seven-member ring construction, the Suzuki-Miyaura cross-coupling reaction for the installation of the double bond and Katsuki-Sharpless asymmetric epoxidation for the introduction of chiral centers. The first total synthesis and absolute configuration assignment of heterocornol D ( 3a ) were achieved. Four stereoisomers, 3a , ent - 3a , 3b and ent - 3b , of this natural polyketide were prepared, starting with 2,6-dihydroxy benzoic acid and divinyl carbinol. The absolute and relative configuration of heterocornol D was assigned via single-crystal X-ray analysis. The extension of the described synthetic approach is further presented with the synthesis of heterocornol C by applying the ether group reduction method to the lactone.
Keyphrases
  • ms ms
  • high resolution
  • magnetic resonance imaging
  • computed tomography
  • ionic liquid
  • mass spectrometry