title: (E)-β-borylstyrene in the Diels-Alder reaction with 3,5-dibromo-2-pyrone for the syntheses of (±)-1-epi-pancratistatin and (±)- pancratistatin.
abstract: New synthetic routes to (±)-1-epi-pancratistatin and (±)-pancratistatin were devised using (E)-β-borylstyrene as a dienophile for the key Diels-Alder reaction with 3,5-dibromo-2-pyrone. The boronate in the cycloadduct was oxidized to provide the pivotal C1-hydroxyl group of the titled compounds.
authors.affiliation: Department of Chemistry, Hanyang University , Seoul, Korea 133-791.
authors.forename: Hyun-Kyu
authors.initials: HK
authors.lastname: Cho
authors.forename: Hwa-Yeon
authors.initials: HY
authors.lastname: Lim
authors.forename: Cheon-Gyu
authors.initials: CG
authors.lastname: Cho
mesh_terms: D047151:Amaryllidaceae Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D061565:Cycloaddition Reaction; D007546:Isoquinolines / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010084:Oxidation-Reduction; D011753:Pyrones / Q000737:chemistry*
chemical_list: C450850:3,5-dibromo-2-pyrone; D047151:Amaryllidaceae Alkaloids; D007546:Isoquinolines; D011753:Pyrones; C044997:pancratistatin