title: Total synthesis of (+)-vibsanin A.
abstract: The first total synthesis of (+)-vibsanin A, an 11-membered vibsane diterpenoid, was achieved, unambiguously establishing its relative and absolute stereochemistry. Highlights of the synthesis include the stereoselective formation of an all-carbon quaternary stereocenter by a zinc-mediated Barbier-type allylation in an aqueous medium, and the efficient construction of an 11-membered ring skeleton by a combination of an intramolecular Nozaki-Hiyama-Kishi (NHK) reaction and a Mitsunobu reaction.
authors.affiliation: Department of Applied Chemistry, Keio University , Hiyoshi, Kohoku-ku, Yokohama 223-8522, Japan.
authors.forename: Ken-ichi
authors.initials: K
authors.lastname: Takao
authors.forename: Kohei
authors.initials: K
authors.lastname: Tsunoda
authors.forename: Takuya
authors.initials: T
authors.lastname: Kurisu
authors.forename: Akihiro
authors.initials: A
authors.lastname: Sakama
authors.forename: Yoshiyasu
authors.initials: Y
authors.lastname: Nishimura
authors.forename: Keisuke
authors.initials: K
authors.lastname: Yoshida
authors.forename: Kin-ichi
authors.initials: K
authors.lastname: Tadano
mesh_terms: D004224:Diterpenes / Q000138:chemical synthesis* / Q000737:chemistry / Q000302:isolation & purification; D015394:Molecular Structure; D013237:Stereoisomerism; D027925:Viburnum / Q000737:chemistry*
chemical_list: D004224:Diterpenes; C000596469:vibsanin A