title: Highly diastereoselective type-I IMDA reaction forming medium-sized macrolactones.
abstract: [Structure: see text] Intramolecular Diels-Alder (IMDA) reactions of 2-pyrones containing an alkyne tether occur with remarkably high diastereofacial selectivity to provide medium-sized macrolactones. Because of the strain in the alkyne-tethered macrocyclic system, a single methyl group in the tether provides sufficient conformational bias to generate medium-sized macrocycles with unusually high selectivity.
authors.affiliation: Department of Chemistry, Hanyang University, 133-791 Seoul, South Korea.
authors.forename: Jeong-Taek
authors.initials: JT
authors.lastname: Shin
authors.forename: Sung-Cho
authors.initials: SC
authors.lastname: Hong
authors.forename: Seunghoon
authors.initials: S
authors.lastname: Shin
authors.forename: Cheon-Gyu
authors.initials: CG
authors.lastname: Cho
mesh_terms: D000480:Alkynes / Q000737:chemistry*; D002384:Catalysis; D018360:Crystallography, X-Ray; D003500:Cyclization; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry; D008968:Molecular Conformation; D015394:Molecular Structure; D011753:Pyrones / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000480:Alkynes; D007783:Lactones; D011753:Pyrones