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Journal de pharmacie de Belgique 02/2003; 58(3):57-74.
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ABSTRACT: This article compiles our results in the field of flavonoid chemistry with the aim to synthesise isotopically labelled products. Two strategies (C6 + C3–C6 vs C6–C2 + C1–C6) and some organometallic (Pd0, MoIV) couplings were explored to build the C6–C3–C6 flavonoid skeleton. Following this work, the gram scale has been reached in addition to the asymmetry of the targeted natural flavan-3-ols, i.e. (+)-catechin, (–)-epicatechin, and (–)-procyanidin B3. These characteristics were necessary in the event of using these molecules for pharmacokinetic and metabolic studies in human beings.
Comptes Rendus Chimie 09/2002; 5(8-9):577–590. · 1.80 Impact Factor
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ABSTRACT: This paper deals with the formal total synthesis of flavonoids bearing the hydroxylation pattern of the catechin series based on an access to the fully functionalized skeleton via the alkylation of phloroglucinol tribenzyl ether by 3,4-dibenzyloxycinnamyl alcohol. This reaction was revealed to be most successful when catalyzed by the Mo(acac)2(SbF6)2 complex. In addition, the underlying concepts to the different ways that can be used in this C6-C3+C6 strategy are discussed.
Tetrahedron Letters 03/2002; 43(15):2675-2678. · 2.68 Impact Factor
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ABSTRACT: Gram amounts of 13C-labelled dimer (-)-procyanidin B3 5 were prepared from 1-[13C]acetic acid by coupling the optically labelled flavan-3,4-diol (+)-7 with protected natural catechin (+)-3 in acidic medium.
Tetrahedron Letters 09/2001; 42(33):5669-5671. · 2.68 Impact Factor
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Tetrahedron Letters 02/2001; 42(7):1279-1281. · 2.68 Impact Factor
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ABSTRACT: Syntheses of 2-phenyl-2H-chromene (3-flavene) and cinnamaldehyde aryloxy-hemiacetal, involving nucleophilic substitution by phenols of the π-allyl palladium complex formed from the acylal of cinnamaldehyde in the presence of catalytic amounts of palladium(0) (10 mol-%), are presented. Alternatively, the corresponding alcohol acetates furnish 1,3-diarylpropenes and cinnamyl aryl ethers. Our results demonstrate the potent C-nucleophilicity of phloroglucinol in Tsuji–Trost reactions in flavonoid synthesis, and again illustrate the already well established O-nucleophilicity of phenols.
European Journal of Organic Chemistry 04/1999; 1999(9):2231-2234. · 3.33 Impact Factor
