Synthesis and Expansion of Bicyclic Enol Ether: A Probable Precursor for the Synthesis of Macrolide (±)-Pyrenophorin

A convenient procedure for the synthesis and expansion of bicyclic rings has been developed for the production of probable precursors of non-racemic pyrenophorin, an antibiotic dilactone. The major highlight for this new synthetic methodology came from the use of a readily available reagent of easy...

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Bibliographic Details
Published in:Journal of the Brazilian Chemical Society 2018-01, Vol.29 (1), p.74-78
Main Authors: Costa, Maísa, Martins, Marcos, de Araújo, Hugo, Resck, Inês
Format: Article
Language:English
Subjects:
CHEMISTRY, MULTIDISCIPLINARY
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Summary:A convenient procedure for the synthesis and expansion of bicyclic rings has been developed for the production of probable precursors of non-racemic pyrenophorin, an antibiotic dilactone. The major highlight for this new synthetic methodology came from the use of a readily available reagent of easy manipulation, 9-oxabicyclo[3.3.1]nonane-2,6-diol, for the preparation of the bicyclic intermediate, which sequentially was subjected to oxidative cleavage with butyl nitrite resulted in an isomeric mixture, a dioximedilactone and diisoxazoledilactone.
ISSN:0103-5053
1678-4790
DOI:10.21577/0103-5053.20170114