title: Total synthesis of an anti-Helicobacter pylori agent, actinopyrone A.
abstract: Actinopyrone A, an anti-Helicobacter pylori agent, was synthesized in nine steps from a silyl dienol ether. A vinylogous anti-aldol was stereoselectively synthesized by our developed remote stereoinduction methodology; coupling of this with a sulfone and a phosphonate species led to the construction of a vinylpyrone compound. This was submitted to reductive de-conjugation to give actinopyrone A. The absolute stereochemistry of actinopyrone A was determined to have the configuration 14R,15R.
authors.affiliation: Department of Applied Chemistry, Faculty of Science and Engineering, Waseda University, 3-4-1 Ohkubo, Shinjuku-ku, Tokyo 169-8555, Japan. seijiro@waseda.jp
authors.forename: Seijiro
authors.initials: S
authors.lastname: Hosokawa
authors.forename: Kazuya
authors.initials: K
authors.lastname: Yokota
authors.forename: Keisuke
authors.initials: K
authors.lastname: Imamura
authors.forename: Yasuaki
authors.initials: Y
authors.lastname: Suzuki
authors.forename: Masataka
authors.initials: M
authors.lastname: Kawarasaki
authors.forename: Kuniaki
authors.initials: K
authors.lastname: Tatsuta
mesh_terms: D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D016480:Helicobacter pylori / Q000187:drug effects*; D008958:Models, Molecular; D015394:Molecular Structure; D011753:Pyrones / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*
chemical_list: D000900:Anti-Bacterial Agents; D011753:Pyrones; C048200:actinopyrone A