title: Stereocontrolled assembly of tetrasubstituted tetrahydrofurans: a concise synthesis of virgatusin.
abstract: The condensation of substituted allylsiloxanes with aldehydes leads to the highly stereoselective construction of 2,3,4,5-tetrasubstituted tetrahydrofurans. With electron-rich aryl and alpha,beta-unsaturated aldehydes as substrates, the stereochemical outcome at C5 can be dictated by appropriate choice of Lewis acid. The reaction has been applied to a concise (nine step) synthesis of (+)-virgatusin (ent-1). [reaction: see text]
authors.affiliation: School of Chemistry, University of Leeds, Leeds LS2 9JT, U.K.
authors.forename: Tito
authors.initials: T
authors.lastname: Akindele
authors.forename: Stephen P
authors.initials: SP
authors.lastname: Marsden
authors.forename: John G
authors.initials: JG
authors.lastname: Cumming
mesh_terms: D000447:Aldehydes / Q000737:chemistry; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry; D017705:Lignans / Q000737:chemistry*; D015394:Molecular Structure; D012833:Siloxanes / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000447:Aldehydes; D005663:Furans; D017705:Lignans; D012833:Siloxanes; C511226:virgatusin