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Synthesis 2001(16): 2463-2469
DOI: 10.1055/s-2001-18711
PAPER
© Georg Thieme Verlag Stuttgart · New York

An Efficient Modular Synthesis of Conjugated ω-(p-Hexyloxyphenyl)-polyenals

Beata W. Domagalskaa, Ludwik Syperb, Kazimiera A. Wilk*a
a Institute of Organic and Polymer Technology, Wrocław University of Technology, Wybrzeře WyspiaŇskiego 27, 50-370 Wrocław, Poland
Fax: +48(71)3203678; e-Mail: kaw@itots.ch.pwr.wroc.pl;
b Institute of Organic Chemistry, Biochemistry and Biotechnology, Wrocław University of Technology, Wybrzeře WyspiaŇskiego 27, 50-370 Wrocław, Poland
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Publication History

Received 6 June 2001
Publication Date:
05 August 2004 (online)

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Abstract

Convenient precursors (α,β-unsaturated aldehydes 1-5) for all-E conjugated ω-(p-hexyloxyphenyl)polyenals having two (15), four (16), five, (19), six (17) and eight (18) conjugated double bonds were synthesized in a modular synthesis using reactive silyl enol ethers [1-(trimethylsilyloxy)-1,3-butadiene or 1-(trimethylsilyloxy)-1,3,5-hexatriene)] as building blocks, and 5,5-diethoxypenta-2-enal (1) as a template. Polyene 8 containing three conjugated double bonds in its structure was obtained from ω-(p-hexyloxyphenyl)propenal (6) and butadienyl ethyl ether as starting materials.

Key words

acetals - aldehydes - aldol reactions - alkenes - eliminations