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Formal synthesis of strobilurins A and X

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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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Authors and Affiliations

  1. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991, Moscow, Russian Federation

    N. Ya. Grigorieva, V. A. Popovsky, A. V. Stepanov & E. D. Lubuzh

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  1. N. Ya. Grigorieva
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  2. V. A. Popovsky
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  3. A. V. Stepanov
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  4. E. D. Lubuzh
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Correspondence to N. Ya. Grigorieva.

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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 11, pp. 2033–2040, November, 2010.

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Grigorieva, N.Y., Popovsky, V.A., Stepanov, A.V. et al. Formal synthesis of strobilurins A and X. Russ Chem Bull 59, 2086–2093 (2010). https://doi.org/10.1007/s11172-010-0359-x

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  • DOI: https://doi.org/10.1007/s11172-010-0359-x

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