Pyridinedithioesters as heterodienophiles: application to the synthesis of aprikalim.
[reaction: see text] Pyridinedithioesters can be used as efficient heterodienophiles when activated by complexation with BF(3), by protonation, or by oxidation of the nitrogen atom of the pyridine moiety. The hetero-Diels-Alder reaction using 3-pyridinedithioester as a heterodienophile was the key step in a new synthesis of Aprikalim in racemic form. The methodology can be reliably extended to prepare new analogues of Aprikalim.
Bastin
Reyhan
R
Laboratoire de Chimie Moléculaire et Thio-Organique (UMR CNRS 6507), ENSICAEN, Université de Caen, 6, Bd. Maréchal Juin, 14050 Caen, France.
Albadri
Hashim
H
Gaumont
Annie-Claude
AC
Gulea
Mihaela
M
D002384:Catalysis; D004952:Esters; D015394:Molecular Structure; D010847:Picolines / Q000138:chemical synthesis*; D011108:Polymers / Q000138:chemical synthesis / Q000737:chemistry; D011714:Pyrans / Q000138:chemical synthesis*; D011725:Pyridines / Q000737:chemistry*
D004952:Esters; D010847:Picolines; D011108:Polymers; D011714:Pyrans; D011725:Pyridines; C061043:aprikalim