Synthesis of pulvinic derivatives via TBAF-mediated regioselective opening of an unsymmetrical monoaromatic pulvinic dilactone.
The synthesis of the monoaromatic pulvinic dilactone 1 from a tetronic acid derivative is reported. The reaction of 1 with various amines was found to provide the two pulvinamides regioisomers 2a and 2b. Using tetrabutylammonium fluoride (TBAF) as an activator, pulvinamides 2a could be obtained with excellent regioselectivities and good yields. Additions of alcohols to 1 are also studied, leading to similar observations.
Habrant
Damien
D
Laboratoire de Synthèse Bio-Organique, CNRS-UMR 7175/LC1, Institut Gilbert Laustriat, Faculté de Pharmacie, Illkirch, 67401 France.
Le Roux
Antoine
A
Poigny
Stéphane
S
Meunier
Stéphane
S
Wagner
Alain
A
Mioskowski
Charles
C
D000438:Alcohols / Q000737:chemistry; D000577:Amides / Q000737:chemistry; D000588:Amines / Q000737:chemistry*; D000975:Antioxidants / Q000737:chemistry; D002264:Carboxylic Acids / Q000138:chemical synthesis / Q000737:chemistry*; D002625:Chemistry, Organic / Q000379:methods*; D005663:Furans / Q000737:chemistry*; D006868:Hydrolysis; D007783:Lactones / Q000138:chemical synthesis / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008956:Models, Chemical; D000644:Quaternary Ammonium Compounds / Q000737:chemistry*; D012997:Solvents / Q000737:chemistry; D013696:Temperature
D000438:Alcohols; D000577:Amides; D000588:Amines; D000975:Antioxidants; D002264:Carboxylic Acids; D005663:Furans; D007783:Lactones; D000644:Quaternary Ammonium Compounds; D012997:Solvents; C009405:tetrabutylammonium; C003422:tetronic acid; C492654:pulvinic acid