- DDQ-mediated oxidation of allylarenes: Expedient access to cinnamaldehyde-containing phenylpropanoids
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Phenylpropanoid natural products containing a cinnamaldehyde motif were easily synthesized from allylarenes mediated by 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) oxidation. Representative examples described herein are five types of 4-hydroxycinnamaldehyde derivatives from monolignols biosynthesis, Boropinal C, and 7-methoxywutaifuranal from plant extracts. Especially, simple synthesis of 7-methoxywutaifuranal was exploited through selective mono-oxidation and subsequent isomerization-ring-closing-metathesis strategy.
- Jiang, Tao-Shan,Zhang, Qingqing,Li, Guohui,Cheng, Xi,Cai, Yongping
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p. 4611 - 4616
(2019/02/01)
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- Synthesis of new biosynthetically important diarylheptanoids and their oxa- and fluoro-analogues by three different strategies
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Wittig, aldol and Wittig-Horner reactions have been used to synthesize new diarylheptanoids, which are putative intermediates in phenylphenalenone biosynthesis in plants. The Wittig-Horner approach was most suitable and gave significantly higher yields in comparison with other methods.
- Baranovsky, Alexander,Schmitt, Bettina,Fowler, Daniel J.,Schneider, Bernd
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p. 1019 - 1045
(2007/10/03)
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- Phase transfer Wittig reaction with 1,3-dioxolan-2-yl-methyltriphenyl phosphonium salts: An efficient method for vinylogation of aromatic aldehydes
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Aldehydes were efficiently transformed into allylic dioxolanes by a Wittig-type reaction, using 1,3-dioxolan-2-yl-methyltriphenylphosphonium bromide under phase transfer conditions. The substituent kinetic effects were studied, and related to Hammett values and electrochemical potentials.
- Daubresse, Nicolas,Francesch, Charlette,Rolando, Christian
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p. 10761 - 10770
(2007/10/03)
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- A mild synthesis of coumaryl, coniferyl, sinapyl aldehydes and alcohols
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Acetylconiferyl aldehyde is obtained from acetylvanillin by a Wittig reaction under phase-transfer conditions; basic hydrolysis gives coniferyl aldehyde, or after reduction with sodium borohydride affords coniferyl alcohol. This method is extended to the sinapyl and coumaryl series.
- Daubresse,Francesch,Mhamdi,Rolando
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p. 369 - 371
(2007/10/02)
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