New Approach for the Stereoselective Synthesis of (+)-epi-Cytoxazone

The stereoselective total synthesis of (+)-epi-cytoxazone was performed satisfactorily in 8 steps, in 17% overall yield, via a novel route from 2,3-O-(3-pentylidene)-(R)-glyceraldehyde. The bulky group alkene-ketal allowed intramolecular control of the target molecule's asymmetric centers in th...

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Bibliographic Details
Published inJournal of the Brazilian Chemical Society Vol. 30; no. 3; pp. 585 - 591
Main Authors Miranda, Izabel L., Sartori, Suelen K., Diaz, Marisa A. N., Diaz-Munoz, Gaspar
Format Journal Article
LanguageEnglish
Published SAO PAULO Soc Brasileira Quimica 01.03.2019
Sociedade Brasileira de Química
Subjects
Chemistry
CHEMISTRY, MULTIDISCIPLINARY
Physical Sciences
Science & Technology
stereoselective dihydroxylation
epi-cytoxazone
Wittig olefination
cytoxazone
RING
2,3-O-(3-pentylidene)-(R)-glyceraldehyde
CYTOKINE MODULATOR
VERSATILE SYNTHESIS
OXAZOLIDINONES
(-)-CYTOXAZONE
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Summary:The stereoselective total synthesis of (+)-epi-cytoxazone was performed satisfactorily in 8 steps, in 17% overall yield, via a novel route from 2,3-O-(3-pentylidene)-(R)-glyceraldehyde. The bulky group alkene-ketal allowed intramolecular control of the target molecule's asymmetric centers in the dihydroxylation step by promoting the approach of OsO4 to the face opposite to that of the ketal group.
ISSN:0103-5053
1678-4790
1678-4790
DOI:10.21577/0103-5053.20180212