Extension of the J-Based Configuration Analysis to Multiple Conformer Equilibria: An Application to Sapinofuranone A
- 13 July 2002
- journal article
- letter
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 4 (16), 2779-2782
- https://doi.org/10.1021/ol026310z
Abstract
A new strategy that extends the application of the J-based configuration analysis to systems characterized by multiple conformer equilibria is described and applied to sapinofuranone A (1), a phytotoxic molecule produced by three strains of Sphaeropsis sapinea. This method, based on a combination of computational techniques and NMR spectroscopy, uses ab initio calculations to predict a set of theoretical homo- and heteronuclear J values which can be compared against experimental NMR data.Keywords
This publication has 10 references indexed in Scilit:
- Amphidinolide W, a New 12-Membered Macrolide from Dinoflagellate Amphidinium sp.The Journal of Organic Chemistry, 2002
- Stereochemical studies on ascaulitoxin: a J-based NMR configurational analysis of a nitrogen substituted systemTetrahedron Letters, 2001
- Total Structure Determination of Apratoxin A, a Potent Novel Cytotoxin from the Marine Cyanobacterium Lyngbya majusculaJournal of the American Chemical Society, 2001
- Angular dependence of spin–spin coupling constantsProgress in Nuclear Magnetic Resonance Spectroscopy, 2000
- Absolute Configuration of Aflastatin A, a Specific Inhibitor of Aflatoxin Production by Aspergillus parasiticusThe Journal of Organic Chemistry, 1999
- Sapinofuranones A and B, Two New 2(3H)-Dihydrofuranones Produced by Sphaeropsis sapinea, a Common Pathogen of ConifersJournal of Natural Products, 1999
- Stereochemical Determination of Acyclic Structures Based on Carbon−Proton Spin-Coupling Constants. A Method of Configuration Analysis for Natural ProductsThe Journal of Organic Chemistry, 1999
- 13C−1H Spin-Coupling Constants in the β-d-Ribofuranosyl Ring: Effect of Ring Conformation on Coupling MagnitudesJournal of the American Chemical Society, 1996
- HETLOC, an Efficient Method for Determining Heteronuclear Long‐Range Couplings with Heteronuclei in Natural AbundanceAngewandte Chemie International Edition in English, 1991
- The relationship between proton-proton NMR coupling constants and substituent electronegativities—ITetrahedron, 1980