Enantiodivergent total synthesis of trioxilins B 3 using Sharpless asymmetric olefin dihydroxylation

The unknown 11,12- threo-stereoisomers of B-type trioxilins, (10 R, 11 R, 12 S)-TrXB3, its (10 S)-epimer and their enantiomers were synthesized (as methyl esters) from a common racemic precursor, viz., methyl rac-10-hydroxyeicos-11( E)-ene-5,8,14-triynoate, by Sharpless enantiodirected dihydroxylati...

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Bibliographic Details
Published in:Mendeleev communications 2004-11, Vol.14 (6), p.287-290
Main Authors: Lapitskaya, Margarita A., Vasiljeva, Ljudmila L., Demin, Peter M., Pivnitsky, Kasimir K.
Format: Article
Language:English
Online Access:Get full text
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Summary:The unknown 11,12- threo-stereoisomers of B-type trioxilins, (10 R, 11 R, 12 S)-TrXB3, its (10 S)-epimer and their enantiomers were synthesized (as methyl esters) from a common racemic precursor, viz., methyl rac-10-hydroxyeicos-11( E)-ene-5,8,14-triynoate, by Sharpless enantiodirected dihydroxylation of the double bond as the key step.
ISSN:0959-9436
DOI:10.1070/MC2004v014n06ABEH002003