Formal synthesis of strobilurins A and X
Тип публикации: Journal Article
Дата публикации: 2010-11-01
scimago Q3
БС2
SJR: 0.305
CiteScore: 2.8
Impact factor: 1.7
ISSN: 10665285, 15739171
General Chemistry
Краткое описание
Known synthetic precursors of strobilurins A and X, i.e., methyl (3Z,5E)-6-aryl-3-methylhexa-3,5-dienoates (aryl is phenyl, 4-methoxyphenyl), were synthesized by highly stereospecific reactions from 2-(2-tert-butyldimethylsilyloxyethyl)- and 2-[2-(4-methoxybenzyloxy)-ethyl]-5-arylpenta-2E,4E-dien-1-ols. These dienols were efficiently dehydroxylated to (1E,3Z)-4-methyl-6-(4-methoxybenzyloxy)hexa-1,3-dienylarenes with their subsequent demethoxyben-zylation to (3Z,5E)-6-aryl-3-methylhexa-3,5-dien-1-ols. The latter through the step of corresponding aryldienals and aryldienoic acids were transformed to the target methyl (3Z,5E)-6-aryl-3-methylhexa-3,5-dienoates, which completes a formal synthesis of strobilurins A and X. Configuration of the C=C bonds of the conjugated aryldiene system is preserved in the considered transformations by 95–97%.
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Grigorieva N. Ya. et al. Formal synthesis of strobilurins A and X // Russian Chemical Bulletin. 2010. Vol. 59. No. 11. pp. 2086-2093.
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Grigorieva N. Ya., Popovsky V. A., Stepanov A. V., Lubuzh E. D. Formal synthesis of strobilurins A and X // Russian Chemical Bulletin. 2010. Vol. 59. No. 11. pp. 2086-2093.
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TY - JOUR
DO - 10.1007/s11172-010-0359-x
UR - https://doi.org/10.1007/s11172-010-0359-x
TI - Formal synthesis of strobilurins A and X
T2 - Russian Chemical Bulletin
AU - Grigorieva, N Ya
AU - Popovsky, V A
AU - Stepanov, A. V.
AU - Lubuzh, E D
PY - 2010
DA - 2010/11/01
PB - Springer Nature
SP - 2086-2093
IS - 11
VL - 59
SN - 1066-5285
SN - 1573-9171
ER -
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@article{2010_Grigorieva,
author = {N Ya Grigorieva and V A Popovsky and A. V. Stepanov and E D Lubuzh},
title = {Formal synthesis of strobilurins A and X},
journal = {Russian Chemical Bulletin},
year = {2010},
volume = {59},
publisher = {Springer Nature},
month = {nov},
url = {https://doi.org/10.1007/s11172-010-0359-x},
number = {11},
pages = {2086--2093},
doi = {10.1007/s11172-010-0359-x}
}
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MLA
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Grigorieva, N. Ya., et al. “Formal synthesis of strobilurins A and X.” Russian Chemical Bulletin, vol. 59, no. 11, Nov. 2010, pp. 2086-2093. https://doi.org/10.1007/s11172-010-0359-x.