title: Total synthesis of (-)-dihydrosporothriolide utilizing an indium-mediated Reformatsky-Claisen rearrangement.
abstract: The asymmetric synthesis of (-)-dihydrosporothriolide (1), a biologically active bis-γ-butyrolactone, is described, that proceeds through a D-proline-catalyzed asymmetric aminooxylation, indium-mediated Reformatsky-Claisen rearrangement of an α,α-dibromoacetate derivative, and diastereoselective dihydroxylation. The route requires no protective group manipulation and allows the concise seven-step synthesis of 1 from n-octanal.
authors.affiliation: Graduate School of Biomedical Sciences, Nagasaki University , 1-14 Bunkyo-machi, Nagasaki 852-8521, Japan.
authors.forename: Jun
authors.initials: J
authors.lastname: Ishihara
authors.forename: Hiroaki
authors.initials: H
authors.lastname: Tsuru
authors.forename: Susumi
authors.initials: S
authors.lastname: Hatakeyama
mesh_terms: D015107:4-Butyrolactone / Q000737:chemistry*; D000447:Aldehydes / Q000737:chemistry*; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry*; D007204:Indium / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000447:Aldehydes; D005663:Furans; D007204:Indium; C086157:sporothriolide; D015107:4-Butyrolactone; C031639:caprylic aldehyde