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    Synthesis of a Family of Spirocyclic Scaffolds; Building Blocks for the Exploration of Chemical Space

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    Issue Date
    2013-07-05
    Author
    Kumar, Sarvesh
    Thornton, Paul
    Painter, Thomas O.
    Jain, Prashi
    Downard, Jared
    Douglas, Justin T.
    Santini, Conrad
    Publisher
    American Chemical Society
    Type
    Article
    Article Version
    Scholarly/refereed, author accepted manuscript
    Rights
    This document is the Accepted Manuscript version of a Published Work that appeared in final form in the Journal of Organic Chemistry, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see http://dx.doi.org/10.1021/jo400738b.
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    Abstract
    This report describes the preparation of a series of 17 novel racemic spirocyclic scaffolds that are intended for the creation of compound libraries by parallel synthesis for biological screening. Each scaffold features two points of orthogonal diversification. The scaffolds are related to each other in four ways:

    Through stepwise changes in the size of the nitrogen bearing ring. Through the oxidation state of the carbon centered point of diversification. Through the relative stereochemical orientation of the two diversification sites in those members that are stereogenic. Through the provision of both saturated and unsaturated versions of the furan ring in the scaffold series derived from 3-piperidone.

    The scaffolds provide incremental changes in the relative orientation of the diversity components that would be introduced onto them. The scaffolds feature high sp3 carbon content which is essential for the three dimensional exploration of chemical space. This characteristic is particularly evident in those members of this family that bear two stereocenters, i.e. the two series derived from 3-piperidone and 3-pyrrolidinone. In the series derived from 3-piperidone we were able to “split the difference” between the two diastereomers by preparation of their corresponding unsaturated version.
    URI
    http://hdl.handle.net/1808/23694
    DOI
    https://doi.org/10.1021/jo400738b
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    • Molecular Structures Group [12]
    Citation
    Kumar, S., Thornton, P., Painter, T. O., Jain, P., Downard, J., Douglas, J. T., & Santini, C. (2013). Synthesis of a Family of Spirocyclic Scaffolds; Building Blocks for the Exploration of Chemical Space. The Journal of Organic Chemistry, 78(13), 6529–6539. http://doi.org/10.1021/jo400738b

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    Contact KU ScholarWorks
    785-864-8983
    KU Libraries
    1425 Jayhawk Blvd
    Lawrence, KS 66045
    785-864-8983

    KU Libraries
    1425 Jayhawk Blvd
    Lawrence, KS 66045
    Image Credits
     

     

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