Synthetic study of natural metabolites containing a benzo[c]oxepine skeleton: heterocornol C and D

0573651 - FZÚ 2024 RIV CH eng J - Journal Article
Gettler, J. - Čarný, T. - Markovič, M. - Koóš, P. - Samoľová, Erika - Moncol, J. - Gracza, T.
Synthetic study of natural metabolites containing a benzo[c]oxepine skeleton: heterocornol C and D.
International Journal of Molecular Sciences. Roč. 24, č. 12 (2023), č. článku 10331. ISSN 1661-6596
R&D Projects: GA MŠMT LM2018110
Institutional support: RVO:68378271
Keywords : heterocornol * polyketide * benzo[c]oxepin-1-one * natural compound * symmetric synthesis
OECD category: Condensed matter physics (including formerly solid state physics, supercond.)
Impact factor: 5.6, year: 2022
Method of publishing: Open access

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 po lyketide 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.
Permanent Link: https://hdl.handle.net/11104/0344050