title: Skeletal diversification via heteroatom linkage control: preparation of bicyclic and spirocyclic scaffolds from N-substituted homopropargyl alcohols.
abstract: The discovery and application of a new branching pathway synthesis strategy that rapidly produces skeletally diverse scaffolds is described. Two different scaffold types, one a bicyclic iodo-vinylidene tertiary amine/tertiary alcohol and the other, a spirocyclic 3-furanone, are each obtained using a two-step sequence featuring a common first step. Both scaffold types lead to intermediates that can be orthogonally diversified using the same final components. One of the scaffold types was obtained in sufficiently high yield that it was immediately used to produce a 97-compound library.
authors.affiliation: Center for Chemical Methodologies and Library Development, The University of Kansas, 2034 Becker Drive, Lawrence, Kansas 66047, USA.
authors.forename: Thomas O
authors.initials: TO
authors.lastname: Painter
authors.forename: Jonathon R
authors.initials: JR
authors.lastname: Bunn
authors.forename: Frank J
authors.initials: FJ
authors.lastname: Schoenen
authors.forename: Justin T
authors.initials: JT
authors.lastname: Douglas
authors.forename: Victor W
authors.initials: VW
authors.lastname: Day
authors.forename: Conrad
authors.initials: C
authors.lastname: Santini
mesh_terms: D000480:Alkynes / Q000737:chemistry*; D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000737:chemistry*; D015394:Molecular Structure; D020005:Propanols / Q000737:chemistry*; D013141:Spiro Compounds / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000480:Alkynes; D019086:Bridged Bicyclo Compounds, Heterocyclic; D020005:Propanols; D013141:Spiro Compounds; C028255:propargyl alcohol