title: Diastereoselective preparation of substituted delta-valerolactones. synthesis of (3R,4S)- and (3R,4R)-simplactones.
abstract: The syntheses of simplactones (3R,4S)-1 and (3R,4R)-2 were achieved in 5 steps from N-acyl thiazolidinethione chiral auxiliaries. The syntheses feature a double diastereoselective acetate aldol reaction solely controlled by the chirality of the auxiliary. Highly diastereoselective aldol reactions with s-trioxane were also achieved with N-acyl thiazolidinethione auxiliaries and the stereochemistry of an aldol product confirmed by X-ray analysis.
authors.affiliation: Division of Medicinal and Natural Products Chemistry, The University of Iowa, Iowa City, Iowa 52242, USA.
authors.forename: Antonio
authors.initials: A
authors.lastname: Osorio-Lozada
authors.forename: Horacio F
authors.initials: HF
authors.lastname: Olivo
mesh_terms: D000447:Aldehydes / Q000138:chemical synthesis; D003500:Cyclization; D007783:Lactones / Q000138:chemical synthesis*; D011753:Pyrones / Q000138:chemical synthesis*; D013237:Stereoisomerism
chemical_list: D000447:Aldehydes; D007783:Lactones; D011753:Pyrones; C052207:delta-valerolactone