title: Short asymmetric synthesis of (-)- and (+)-cis-lauthisan.
abstract: The asymmetric synthesis of both enantiomers of cis-lauthisan (3) is achieved in only six steps from diethyl pimelate (4), the key steps being the diastereodivergent reduction of beta-ketosulfoxide 7 and the highly cis-stereoselective Et(3)SiH/TMSOTf-promoted reductive cyclization of enantiopure hydroxy sulfinyl ketones (S)-14 and (R)-14.
authors.affiliation: Departamento de Química Orgánica (C-I), Universidad Autónoma de Madrid, Cantoblanco, Spain. carmen.carreno@uam.es
authors.forename: M Carmen
authors.initials: MC
authors.lastname: Carreño
authors.forename: Renaud
authors.initials: R
authors.lastname: Des Mazery
authors.forename: Antonio
authors.initials: A
authors.lastname: Urbano
authors.forename: Françoise
authors.initials: F
authors.lastname: Colobert
authors.forename: Guy
authors.initials: G
authors.lastname: Solladié
mesh_terms: D003500:Cyclization; D004988:Ethers, Cyclic / Q000138:chemical synthesis / Q000737:chemistry; D044722:Laurencia / Q000737:chemistry; D015394:Molecular Structure; D010084:Oxidation-Reduction; D013237:Stereoisomerism
chemical_list: D004988:Ethers, Cyclic; C471499:lauthisan