The unknown 11,12-threo-stereoisomers of B-type trioxilins, (10R,11R,12S)-TrXB3, its (10S)-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.
Enantiodivergent total synthesis of trioxilins B3 using Sharpless asymmetric olefin dihydroxylation
M. A. Lapitskaya, L. L. Vasiljeva, P. M. Demin and K. K. Pivnitsky, Mendeleev Commun., 2004, 14, 287 DOI: 10.1070/MC2004v014n06ABEH002003
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