M. A. Lapitskaya, L. L. Vasiljeva, P. M. Demin, K. K. Pivnitsky, “Enantiodivergent total synthesis of trioxilins B<sub>3</sub> using Sharpless asymmetric olefin dihydroxylation”, Mendeleev Commun., 2004, Volume 14, Issue 6,Pages <nobr>287

This article is cited in 4 papers

Enantiodivergent total synthesis of trioxilins B₃ using Sharpless asymmetric olefin dihydroxylation

M. A. Lapitskaya, L. L. Vasiljeva, P. M. Demin, K. K. Pivnitsky

N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russian Federation

Abstract: 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.

Language: English

DOI: 10.1070/MC2004v014n06ABEH002003