title: Total synthesis of (±)-hippolachnin A.
abstract: The first total synthesis of the marine polyketide (±)-hippolachnin A has been achieved in nine linear steps and an overall yield of 9%. Rapid access to the oxacyclobutapentalene core structure was secured by strategic application of an ene cyclization.
authors.affiliation: Laboratorium für Organische Chemie, ETH Zürich, HCI H335, Vladimir-Prelog-Weg 3, 8093 Zürich (Switzerland) http://www.carreira.ethz.ch.
authors.forename: Stefan A
authors.initials: SA
authors.lastname: Ruider
authors.forename: Tobias
authors.initials: T
authors.lastname: Sandmeier
authors.forename: Erick M
authors.initials: EM
authors.lastname: Carreira
mesh_terms: D002384:Catalysis; D056831:Coordination Complexes / Q000737:chemistry; D003500:Cyclization; D003503:Cyclobutanes / Q000737:chemistry; D003517:Cyclopentanes / Q000737:chemistry; D007700:Kinetics; D061065:Polyketides / Q000138:chemical synthesis* / Q000737:chemistry; D012238:Rhodium / Q000737:chemistry; D013237:Stereoisomerism; D013816:Thermodynamics
chemical_list: D056831:Coordination Complexes; D003503:Cyclobutanes; D003517:Cyclopentanes; D061065:Polyketides; C585986:hippolachnin A; C024646:pentalenene; D012238:Rhodium
keywords: ene reaction; hippolachnin A; natural products; photochemistry; total synthesis