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Remote stereocontrol in [3,3]-sigmatropic rearrangements: Application to the total synthesis of the immunosuppressant mycestericin G


Reference:

Fairhurst, N. W. G., Mahon, M. F., Munday, R. H. and Carbery, D. R., 2012. Remote stereocontrol in [3,3]-sigmatropic rearrangements: Application to the total synthesis of the immunosuppressant mycestericin G. Organic Letters, 14 (3), pp. 756-759.

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    Official URL:

    http://dx.doi.org/10.1021/ol203300k

    Abstract

    The Ireland - Claisen [3,3]-sigmatropic rearrangement has been used to access biologically important β,β′-dihydroxy α-amino acids. The rearrangement reported is highly stereoselective and offers excellent levels of remote stereocontrol. This strategy has been used to synthesize the natural immunosuppressant mycestericin G and ent-mycestericin G, allowing for a revision of absolute configuration of this natural product.

    Details

    Item Type Articles
    CreatorsFairhurst, N. W. G., Mahon, M. F., Munday, R. H. and Carbery, D. R.
    DOI10.1021/ol203300k
    DepartmentsFaculty of Science > Chemistry
    Publisher StatementCarbery_Organic-Letters_2012_14_3_756.pdf: This document is the Accepted Manuscript version of a Published Work that appeared in final form in Organic Letters, 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/ol203300k; Carbery_Organic-Letters_2012_14_3_756.doc: This document is the Accepted Manuscript version of a Published Work that appeared in final form in Organic Letters, 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/ol203300k
    RefereedYes
    StatusPublished
    ID Code29113

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