Work

Skeletal Diversification via Heteroatom Linkage Control: Preparation of Bicyclic and Spirocyclic Scaffolds from N-Substituted Homopropargyl Alcohols

Year: 2013

Type: article

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.

Source: The Journal of Organic Chemistry

DOI: 10.1021/jo400077m

Authors: Thomas O. Painter, Jonathon R. Bunn, Frank J. Schoenen, Justin T. Douglas, Victor W. Day, Conrad Santini

Institution: University of Kansas

Language: English

Topic: Organic Chemistry Synthesis Methods

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funders: National Institute of General Medical Sciences, National Center for Research Resources

Awards: Center of Excellence in Chemical Methodologies and Library Development, Avance II 500 High Performance Digital NMR Spectrometer System