title: β-Silyl styrene as a dienophile in the cycloaddition with 3,5-dibromo-2-pyrone for the total synthesis of (±)-pancratistatin.
abstract: A new synthetic route to (±)-pancratistatin was devised utilizing β-silyl styrene as a dienophile in the cycloaddition with 3,5-dibromo-2-pyrone. The TMS group incorporated in the cycloadduct permitted a facile elimination process for the eventual installation of the C(1)-OH function. Subsequent transformations including Curtius rearrangement and Bischler-Napieralski reactions completed the total synthesis of (±)-pancratistatin.
authors: Department of Chemistry, Hanyang University, Seoul, Korea 133-791.
authors: Yong-Geun
authors: YG
authors: Jung
authors: Ho-Ung
authors: HU
authors: Kang
authors: Hyun-Kyu
authors: HK
authors: Cho
authors: Cheon-Gyu
authors: CG
authors: Cho
mesh_terms: D047151:Amaryllidaceae Alkaloids / Q000138:chemical synthesis*; D003500:Cyclization; D007546:Isoquinolines / Q000138:chemical synthesis*; D015394:Molecular Structure; D011753:Pyrones / Q000737:chemistry*; D012825:Silicon / Q000737:chemistry*; D020058:Styrene / Q000737:chemistry*
chemical_list: C450850:3,5-dibromo-2-pyrone; D047151:Amaryllidaceae Alkaloids; D007546:Isoquinolines; D011753:Pyrones; D020058:Styrene; C044997:pancratistatin; D012825:Silicon