title: De novo asymmetric synthesis of anamarine and its analogues.
abstract: [reaction: see text] The enantioselective synthesis of anamarine has been achieved in 21 steps. The route relies on enantio- and regioselective Sharpless dihydroxylation of dienoate ester and zinc borohydride reduction to establish the C-8-C-11 stereochemistry. A diastereoselective Leighton allylation established the desired C-5 stereochemistry. The route has also been used to prepare two diastereoisomers of anamarine in 14 steps.
authors.affiliation: Department of Chemistry, West Virginia University, Morgantown, West Virginia 26506, USA.
authors.forename: Dong
authors.initials: D
authors.lastname: Gao
authors.forename: George A
authors.initials: GA
authors.lastname: O'Doherty
mesh_terms: D015394:Molecular Structure; D011753:Pyrones / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D011753:Pyrones; C506157:anamarine