gambieric-acid-b and tetrahydrofuran

gambieric-acid-b has been researched along with tetrahydrofuran* in 1 studies

Other Studies

1 other study(ies) available for gambieric-acid-b and tetrahydrofuran

Article	Year
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. The Journal of organic chemistry, 2009, Jun-05, Volume: 74, Issue:11 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 (1)H and (13)C 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 (1)H and (13)C NMR data with those of the natural product. Topics: Antifungal Agents; Biological Products; Ciguatoxins; Ethers, Cyclic; Furans; Magnetic Resonance Spectroscopy; Molecular Structure; Stereoisomerism	2009

Article

Year

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.

The Journal of organic chemistry, 2009, Jun-05, Volume: 74, Issue:11

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 (1)H and (13)C 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 (1)H and (13)C NMR data with those of the natural product.

Topics: Antifungal Agents; Biological Products; Ciguatoxins; Ethers, Cyclic; Furans; Magnetic Resonance Spectroscopy; Molecular Structure; Stereoisomerism

2009