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Issue 4, 2009
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Highly diastereoselective desymmetrisation of cyclic meso-anhydrides and derivatisation for use in natural product synthesis

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Abstract

A new and efficient desymmetrisation of succinic and glutaric cyclic meso-anhydrides is described, providing excellent yields and diastereoselectivities in most cases. Derivatisation of the desymmetrised products is demonstrated by their conversion into mono-protected 1,4-diols. General synthetic utility of the method is established by its application towards a key fragment in the total synthesis of the immunosuppressant antitumour natural product, rapamycin.

Graphical abstract: Highly diastereoselective desymmetrisation of cyclic meso-anhydrides and derivatisation for use in natural product synthesis

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Publication details

The article was received on 04 Aug 2008, accepted on 10 Nov 2008 and first published on 06 Jan 2009


Article type: Paper
DOI: 10.1039/B813494D
Citation: Org. Biomol. Chem., 2009,7, 747-760
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    Highly diastereoselective desymmetrisation of cyclic meso-anhydrides and derivatisation for use in natural product synthesis

    A. C. Evans, D. A. Longbottom, M. Matsuoka, J. E. Davies, R. Turner, V. Franckevičius and S. V. Ley, Org. Biomol. Chem., 2009, 7, 747
    DOI: 10.1039/B813494D

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