title: Pyridinedithioesters as heterodienophiles: application to the synthesis of aprikalim.
abstract: [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.
authors.affiliation: Laboratoire de Chimie Moléculaire et Thio-Organique (UMR CNRS 6507), ENSICAEN, Université de Caen, 6, Bd. Maréchal Juin, 14050 Caen, France.
authors.forename: Reyhan
authors.initials: R
authors.lastname: Bastin
authors.forename: Hashim
authors.initials: H
authors.lastname: Albadri
authors.forename: Annie-Claude
authors.initials: AC
authors.lastname: Gaumont
authors.forename: Mihaela
authors.initials: M
authors.lastname: Gulea
mesh_terms: 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*
chemical_list: D004952:Esters; D010847:Picolines; D011108:Polymers; D011714:Pyrans; D011725:Pyridines; C061043:aprikalim