title: Concise synthesis of spirocyclic, bridged gamma-butyrolactones via stereospecific, dyotropic rearrangements of beta-lactones involving 1,2-acyl and delta-lactone migrations.
abstract: Dyotropic processes involving unprecedented 1,2-acyl migrations provide access to novel spirocyclic, bridged keto-gamma-lactones from a series of fused, tricyclic-beta-lactones, available via biscyclization of ketoacids including a new asymmetric variant. In addition, a spirocyclic bis-gamma-lactone was generated via a dyotropic process involving a 1,2-beta-lactone/sigma-lactone interchange. Overall, this sequence provides a simple, two-step process for conversion of diketoacids to complex spiro[5.n]alkanes bearing a contiguous tertiary carbon center, a quaternary carbon center, and a tertiary alcohol in the form of a bridging gamma-lactone.
authors.affiliation: Department of Chemistry, Texas A&M University, College Station, Texas 77842-3012, USA.
authors.forename: Vikram C
authors.initials: VC
authors.lastname: Purohit
authors.forename: Andrea S
authors.initials: AS
authors.lastname: Matla
authors.forename: Daniel
authors.initials: D
authors.lastname: Romo