title: Total synthesis of (+)-herboxidiene from two chiral lactate-derived ketones.
abstract: A substrate-controlled synthesis of (+)-herboxidiene from two lactate-derived chiral ketones is described. Remarkably, most of the carbon backbone was constructed through highly stereoselective titanium-mediated aldol reactions and an Ireland-Claisen rearrangement. Furthermore, an oxa-Michael cyclization and a high-yield Suzuki coupling were used to assemble the pyran ring and the diene moiety respectively.
authors.affiliation: Departament de Química Orgànica, Universitat de Barcelona, Carrer Martí i Franqués 1-11, 08028 Barcelona, Catalonia, Spain.
authors.forename: Miquel
authors.initials: M
authors.lastname: Pellicena
authors.forename: Katrina
authors.initials: K
authors.lastname: Krämer
authors.forename: Pedro
authors.initials: P
authors.lastname: Romea
authors.forename: Fèlix
authors.initials: F
authors.lastname: Urpí
mesh_terms: D003500:Cyclization; D005233:Fatty Alcohols / Q000138:chemical synthesis*; D007659:Ketones / Q000737:chemistry*; D019344:Lactic Acid / Q000737:chemistry*; D015394:Molecular Structure; D011714:Pyrans / Q000138:chemical synthesis*; D013237:Stereoisomerism
chemical_list: D005233:Fatty Alcohols; D007659:Ketones; D011714:Pyrans; C076087:herboxidiene; D019344:Lactic Acid