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Enantiodivergent total synthesis of trioxilins B3 using Sharpless asymmetric olefin dihydroxylation

Margarita Aleksandrovna Lapitskaya 1
Margarita Aleksandrovna Lapitskaya
, 
Ljudmila Leonidovna Vasiljeva 1
Ljudmila Leonidovna Vasiljeva
, 
Peter Mikhailovich Demin 1
Peter Mikhailovich Demin
, 
Kazimir Konstantinovich Pivnitsky 1
Kazimir Konstantinovich Pivnitsky
10.1070/MC2004v014n06ABEH002003
Published 2004-12-17
Communication , Volume 14, Issue 6, 287-290
4
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Lapitskaya M. A. et al. Enantiodivergent total synthesis of trioxilins B3 using Sharpless asymmetric olefin dihydroxylation // Mendeleev Communications. 2004. Vol. 14. No. 6. pp. 287-290.
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Lapitskaya M. A., Vasiljeva L. L., Demin P. M., Pivnitsky K. K. Enantiodivergent total synthesis of trioxilins B3 using Sharpless asymmetric olefin dihydroxylation // Mendeleev Communications. 2004. Vol. 14. No. 6. pp. 287-290.
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TY - JOUR
DO - 10.1070/MC2004v014n06ABEH002003
UR - https://mendcomm.colab.ws/publications/10.1070/MC2004v014n06ABEH002003
TI - Enantiodivergent total synthesis of trioxilins B3 using Sharpless asymmetric olefin dihydroxylation
T2 - Mendeleev Communications
AU - Lapitskaya, Margarita Aleksandrovna
AU - Vasiljeva, Ljudmila Leonidovna
AU - Demin, Peter Mikhailovich
AU - Pivnitsky, Kazimir Konstantinovich
PY - 2004
DA - 2004/12/17
PB - Mendeleev Communications
SP - 287-290
IS - 6
VL - 14
ER -
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@article{2004_Lapitskaya,
author = {Margarita Aleksandrovna Lapitskaya and Ljudmila Leonidovna Vasiljeva and Peter Mikhailovich Demin and Kazimir Konstantinovich Pivnitsky},
title = {Enantiodivergent total synthesis of trioxilins B3 using Sharpless asymmetric olefin dihydroxylation},
journal = {Mendeleev Communications},
year = {2004},
volume = {14},
publisher = {Mendeleev Communications},
month = {Dec},
url = {https://mendcomm.colab.ws/publications/10.1070/MC2004v014n06ABEH002003},
number = {6},
pages = {287--290},
doi = {10.1070/MC2004v014n06ABEH002003}
}
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Lapitskaya, Margarita Aleksandrovna, et al. “Enantiodivergent total synthesis of trioxilins B3 using Sharpless asymmetric olefin dihydroxylation.” Mendeleev Communications, vol. 14, no. 6, Dec. 2004, pp. 287-290. https://mendcomm.colab.ws/publications/10.1070/MC2004v014n06ABEH002003.

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.

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