- Synthesis and biological activity of α,β,γ,δ-unsaturated aldehydes from diatoms
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α,β,γ,δ-Unsaturated aldehydes have gained increasing attention since 2,4-decadienal and 2,4,7-decatrienal were isolated from the diatom Thalassiosira rotula and characterized as cell antiproliferative metabolites. Structurally related α,β,γ,δ-unsaturated aldehydes were found in this alga as well as in other diatom species. We present a short and universal synthesis of this compound class along with a structure-activity study of the potential to inhibit sea urchin egg cleavage. Pd0- or CoII-mediated cross coupling of 5-iodo-penta-2,4-dienal with organo-zincates allows the fast and flexible synthesis of numerous aldehydes from this universal precursor. The stereochemistry of the double bond system of the precursor was preserved during the coupling. Bioassays showed that the polarity of the side chain is important for antiproliferative activity with 2,4-decadienal as the most active compound tested compared to the shorter-chain aliphatic homologues and to ω-oxo acids with conjugated double systems. In contrast, the double bond geometry has no influence on biological activity. The α,β-unsaturated 2E-decenal was also highly active, while activity diminished in the case of saturated aldehydes of similar chain length. 1-Decanol, 2-decanone and decanoic acid were not active.
- Adolph, Sven,Poulet, Serge A.,Pohnert, Georg
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p. 3003 - 3008
(2007/10/03)
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- Straightforward preparation of (2E,4Z)-2,4-heptadien-1-ol and (2E,4Z)-2,4-heptadienal
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A concise synthesis of (2E,4Z)-2,4-heptadien-1-ol and (2E,4Z)-2,4-heptadienal is presented. Commercially available (Z)-2-penten-1-ol was converted to ethyl-(2E,4Z)-2,4-heptadienoate by reaction with activated MnO2 and (carboethoxymethylene)triphenylphosphorane in the presence of benzoic acid as a catalyst. Ethyl-(2E,4Z)-2,4-hep-tadienoate was converted to (2E,4Z)-2,4-heptadien-1-ol with LiAlH4. The alcohol was partially oxidized to (2E,4Z)-2,4-heptadienal with MnO2. The title compounds are male-specific, antennally active volatile compounds from the Saltcedar leaf beetle, Diorhabda elongata Brulle (Coleoptera: Chrysomelidae) and have potential use in the biological control of the invasive weed saltcedar (Tamarix spp).
- Petroski, Richard J.
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p. 3233 - 3241
(2007/10/03)
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- (2E)-4,4-dimethoxy-2-butenal in the synthesis of conjugated dienes and dienals
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Using (2E)-4,4-dimethoxy-2-butenal as starting compound, methods were developed for synthesis of (2E,4E)-and (2E,4Z)-dimethoxyalkadienes. Deacetalization of the latter gives with high yield the corresponding dienals which are naturally occurring compounds
- Badanyan,Makaryan,Ovanesyan,Panosyan
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p. 633 - 639
(2007/10/03)
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- A Novel and General Route to 1-Iodo-2,4(E,E)-dienes via Pentadienyl Dithiocarbamate
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The title compounds were prepared from pentadienyl dithiocarbamate via S-methylathion and by use of the iodide an unsymmetric, all-trans-conjugated pentaene was synthesized.
- Hayashi, Toshio,Sasaoka, Kazuo,Oishi, Takeshi
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p. 1362 - 1363
(2007/10/02)
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- HIGHLY STEREOCONTOROLLED SYNTHESIS OF (2E,4Z)-DIENIC ESTERS BY ALUMINA CATALYST
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Thermal treatment of β-allenic esters (2) with alumina catalyst in aprotic solvents yielded (2E,4Z)-dienoic esters (3) in 57-87percent yields with 91-100percent stereoselectivity.
- Tsuboi, Sadao,Masuda, Toshihide,Makino, Hiroshi,Takeda, Akira
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p. 209 - 212
(2007/10/02)
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