Stereochemical Aspects of the Beckman Rearrangement of Oximes of Levoglucosenone and Its Dihydro Derivative. Enantioselective Synthesis of (+)- -Pelargonolactone
Тип публикации: Journal Article
Дата публикации: 2003-11-01
scimago Q3
wos Q4
БС3
SJR: 0.296
CiteScore: 1.3
Impact factor: 0.9
ISSN: 00093130, 15738388
General Chemistry
General Biochemistry, Genetics and Molecular Biology
Plant Science
Краткое описание
Regiospecific C55 -halogenation with retention of configuration occurred upon Beckman fragmentation of levoglucosenone oxime using SOCl2 or PBr3. On the other hand, the oxime of its dihydro derivative gave under these conditions the C6 - substitution product. A stereoselective synthetic scheme for (+)-γ-pelargonolactone, an attractant for the rice and corn weevils Sitophiltus zeamais, was developed from the fragmentation product of levoglucosenone oxime.
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Valeev F. A. et al. Stereochemical Aspects of the Beckman Rearrangement of Oximes of Levoglucosenone and Its Dihydro Derivative. Enantioselective Synthesis of (+)- -Pelargonolactone // Chemistry of Natural Compounds. 2003. Vol. 39. No. 6. pp. 563-568.
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Valeev F. A., Gorobets E. V., Tsypysheva I. P., Singizova G. S., Kalimullina L. Kh., Safarov M. G., Shitikova O. V., Miftakhov M. S. Stereochemical Aspects of the Beckman Rearrangement of Oximes of Levoglucosenone and Its Dihydro Derivative. Enantioselective Synthesis of (+)- -Pelargonolactone // Chemistry of Natural Compounds. 2003. Vol. 39. No. 6. pp. 563-568.
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TY - JOUR
DO - 10.1023/B:CONC.0000018110.36123.f2
UR - http://link.springer.com/10.1023/B:CONC.0000018110.36123.f2
TI - Stereochemical Aspects of the Beckman Rearrangement of Oximes of Levoglucosenone and Its Dihydro Derivative. Enantioselective Synthesis of (+)- -Pelargonolactone
T2 - Chemistry of Natural Compounds
AU - Valeev, F A
AU - Gorobets, E V
AU - Tsypysheva, I P
AU - Singizova, G Sh
AU - Kalimullina, L Kh
AU - Safarov, M G
AU - Shitikova, O V
AU - Miftakhov, M S
PY - 2003
DA - 2003/11/01
PB - Springer Nature
SP - 563-568
IS - 6
VL - 39
SN - 0009-3130
SN - 1573-8388
ER -
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@article{2003_Valeev,
author = {F A Valeev and E V Gorobets and I P Tsypysheva and G Sh Singizova and L Kh Kalimullina and M G Safarov and O V Shitikova and M S Miftakhov},
title = {Stereochemical Aspects of the Beckman Rearrangement of Oximes of Levoglucosenone and Its Dihydro Derivative. Enantioselective Synthesis of (+)- -Pelargonolactone},
journal = {Chemistry of Natural Compounds},
year = {2003},
volume = {39},
publisher = {Springer Nature},
month = {nov},
url = {http://link.springer.com/10.1023/B:CONC.0000018110.36123.f2},
number = {6},
pages = {563--568},
doi = {10.1023/B:CONC.0000018110.36123.f2}
}
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MLA
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Valeev, F. A., et al. “Stereochemical Aspects of the Beckman Rearrangement of Oximes of Levoglucosenone and Its Dihydro Derivative. Enantioselective Synthesis of (+)- -Pelargonolactone.” Chemistry of Natural Compounds, vol. 39, no. 6, Nov. 2003, pp. 563-568. http://link.springer.com/10.1023/B:CONC.0000018110.36123.f2.