Total synthesis of asymmetric flavonoids: The development and applications of 13C-labelling

Bastien Nay; Valérie Arnaudinaud; Joseph Vercauteren

doi:10.1016/S1631-0748(02)01417-0

Total synthesis of asymmetric flavonoids: The development and applications of ¹³C-labelling

Bastien Nay, Valérie Arnaudinaud, Joseph Vercauteren

Research output: Contribution to journal › Article › peer-review

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, Mo^IV) 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.

Original language	English
Pages (from-to)	577-590
Number of pages	14
Journal	Comptes Rendus Chimie
Volume	5
Issue number	8
DOIs	https://doi.org/10.1016/S1631-0748(02)01417-0
Publication status	Published - 1 Jan 2002
Externally published	Yes

Keywords

Bioavailability
C-labelling
Catechin
Flavonoids
Procyanidins
Resolution
Total synthesis

Access to Document

10.1016/S1631-0748(02)01417-0

Cite this

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title = "Total synthesis of asymmetric flavonoids: The development and applications of 13C-labelling",

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.",

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T1 - Total synthesis of asymmetric flavonoids

T2 - The development and applications of 13C-labelling

AU - Nay, Bastien

AU - Arnaudinaud, Valérie

AU - Vercauteren, Joseph

PY - 2002/1/1

Y1 - 2002/1/1

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AB - 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.

KW - Bioavailability

KW - C-labelling

KW - Catechin

KW - Flavonoids

KW - Procyanidins

KW - Resolution

KW - Total synthesis

U2 - 10.1016/S1631-0748(02)01417-0

DO - 10.1016/S1631-0748(02)01417-0

M3 - Article

AN - SCOPUS:0036966572

SN - 1631-0748

VL - 5

SP - 577

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JO - Comptes Rendus Chimie

JF - Comptes Rendus Chimie

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