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Synlett 2008(14): 2083-2086  
DOI: 10.1055/s-2008-1077976
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of Pyrenolide D Analogues

Jeremy Robertson*, Kiri Stevens, Sébastien Naud
Department of Chemistry, Chemistry Research Laboratory, University of Oxford, Mansfield Road, Oxford, OX1 3TA, UK
Fax: +44(1865)285002; e-Mail: jeremy.robertson@chem.ox.ac.uk;
Further Information

Publication History

Received 28 April 2008
Publication Date:
15 July 2008 (online)

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Abstract

We present a short, enantiospecific synthesis of four hydroxylated analogues of pyrenolide D from d-glucose based on furan oxidative spirocyclisation.

Key words

butenolides - furans - lactones - oxidations - spiro compounds

    References and Notes

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7

Lomas, A.; Robertson, J. unpublished results.

15

All reactions were run at 20 ˚C except where stated.

20

NMR assignments are numbered according to carbohydrate conventions (as Figure  [¹] ). Only strong or characterising IR peaks are given.