Formal synthesis of strobilurins A and X |
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Authors: | N Ya Grigorieva V A Popovsky A V Stepanov E D Lubuzh |
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Institution: | 1.N. D. Zelinsky Institute of Organic Chemistry,Russian Academy of Sciences,Moscow,Russian Federation |
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Abstract: | 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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