Stereocontrolled synthesis of (3Z,5E)-6-aryl-3-methylhexa-3,5-dien-1-ols, intermediates in the synthesis of strobilurin antibiotics View Full Text


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Article Info

DATE

2010-04

AUTHORS

N. Ya. Grigorieva, V. A. Popovsky, A. V. Stepanov, N. G. Kolotyrkina

ABSTRACT

(2E,4E)-5-Aryl-2-(2-benzyloxyethyl)penta-2,4-dien-1-als (aryl is phenyl and 4-methox-yphenyl) were reduced with NaBH4 quantitatively and stereospecifically to the corresponding penta-2(E),4(E)-dien-1-ols. The hydroxymethyl group in the latter was transformed into a methyl one with a stereoselectivity of 92–97%. Debenzylation of the resulting (1E,3Z)-1-aryl-6-benzyloxy-4-methylhexa-1,3-dienes with AlCl3 in the presence of PhNMe2 afforded the target (3Z,5E)-6-aryl-3-methylhexa-3,5-dien-1-ols; the configuration of the C=C bonds in the conjugated aryl diene systems was retained at 95%. More... »

PAGES

848-851

Identifiers

URI

http://scigraph.springernature.com/pub.10.1007/s11172-010-0172-6

DOI

http://dx.doi.org/10.1007/s11172-010-0172-6

DIMENSIONS

https://app.dimensions.ai/details/publication/pub.1052889056


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