NMR determination of absolute configuration of butenolides of annonaceous type

Chemistry - A European Journal

Volumn 8, Issue 24, 2002, Pages 5662-5666

  Latypov, Shamil ^b   Franck, Xavier ^a   Jullian, Jean Christophe ^a   Hocquemiller, Reynald ^a   Figadère, Bruno ^a  

^a CNRS   (France)

^b A E ARBUZOV INSTITUTE OF ORGANIC AND PHYSICAL CHEMISTRY   (Russian Federation)

Author keywords

Lactones; Natural products; NMR spectroscopy

Indexed keywords

NUCLEAR MAGNETIC RESONANCE; THERMAL EFFECTS;

CHIRAL SOLVATING AGENTS (CSA);

ORGANIC COMPOUNDS;

ACETOGENIN; BUTENOLIDE; CHEMICAL AGENT; CHEMICAL COMPOUND; FURAN DERIVATIVE; HYDROXYL RADICAL; LACTONE; NATURAL PRODUCT;

ANALYTIC METHOD; ARTICLE; CHEMICAL MODEL; CHEMICAL MODIFICATION; CHEMICAL STRUCTURE; CHIRAL CHROMATOGRAPHY; CONCENTRATION (PARAMETERS); DIASTEREOISOMER; ENANTIOMER; LABORATORY; LOW TEMPERATURE; NUCLEAR MAGNETIC RESONANCE; PROTON NUCLEAR MAGNETIC RESONANCE; SOLVATION;

EID: 0347520940     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/1521-3765(20021216)8:24<5662::AID-CHEM5662>3.0.CO;2-H     Document Type: Article

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34. When squamocin 6a was protected as a trisilylated ether (TBDMSOTf, pyridine, 4-DMAP), the trisilyl ether 6c was, after purification, analyzed as described above for -1. Surprisingly, we observed two peaks at δ = 4.997 and 4.950 ppm in a 15/85 ratio. We can conclude that the protection step occurred with partial epimerization of the butenolide.