title: Catalytic asymmetric synthesis of (+)-anthecotulide using enyne and Meyer-Schuster rearrangements.
abstract: The bioactive sesquiterpene lactone (+)-anthecotulide (1) is synthesized for the first time, in a six-step sequence devoid of protecting groups. The key transformations are a novel Rh(I)-catalyzed asymmetric enyne rearrangement of a terminal alkynyl ester (4), to form the α-methylene-γ-butyrolactone core, and a final-step mild Au(I)-catalyzed Meyer-Schuster rearrangement.
authors: Department of Chemistry, University of Oxford, Chemistry Research Laboratory, Mansfield Road, Oxford, OX1 3TA, UK. david.hodgson@chem.ox.ac.uk
authors: David M
authors: DM
authors: Hodgson
authors: Eric P A
authors: EP
authors: Talbot
authors: Barry P
authors: BP
authors: Clark
mesh_terms: D002384:Catalysis; D003500:Cyclization; D007659:Ketones / Q000737:chemistry*; D007783:Lactones / Q000138:chemical synthesis*; D015394:Molecular Structure; D012717:Sesquiterpenes / Q000138:chemical synthesis*; D013237:Stereoisomerism
chemical_list: D007659:Ketones; D007783:Lactones; D012717:Sesquiterpenes; C499300:anthecotulide