1159986-35-2Relevant academic research and scientific papers
Synthetic studies on gambieric acids, potent antifungal polycyclic ether natural products: Reassignment of the absolute configuration of the nonacyclic polyether core by NMR analysis of model compounds
Fuwa, Haruhiko,Ishigai, Kazuya,Goto, Tomomi,Suzuki, Akihiro,Sasaki, Makoto
experimental part, p. 4024 - 4040 (2009/09/25)
(Chemical Equation Presented) A highly stereocontrolled, convergent synthesis of the A/B-ring fragment of gambieric acids (GAs) has been developed on the basis of (i) a Suzuki-Miyaura coupling of the C1-C6 alkylborate and the C7-C17 vinyl iodide and (ii) a diastereoselective haloetherification for the construction of the A-ring tetrahydrofuran as key steps. Inspection of the 1H and 13C NMR chemical shifts of the synthesized A/B-ring model compounds led to a stereochemical reassignment of the absolute configuration of the polycyclic ether core of GAs. This structure revision was further supported by a synthesis of the A/BC-ring model compound of gambieric acid B and a comparison of its 1H and 13C NMR data with those of the natural product.
