Total synthesis of isotopically labelled flavonoids, 2: 13C-labelled (±)-catechin from potassium [13C]cyanide

Bastien Nay; Valérie Arnaudinaud; Jean François Peyrat; Alain Nuhrich; Gérard Deffieux; Jean Michel Mérillon; Joseph Vercauteren

doi:10.1002/1099-0690(200004)2000:7<1279::aid-ejoc1279>3.0.co;2-d

Total synthesis of isotopically labelled flavonoids, 2: ¹³C-labelled (±)-catechin from potassium [¹³C]cyanide

Bastien Nay, Valérie Arnaudinaud, Jean François Peyrat, Alain Nuhrich, Gérard Deffieux, Jean Michel Mérillon, Joseph Vercauteren

Univ. Bordeaux

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

Abstract

Racemic 4-[¹³C]catechin 14 has been synthesized in ten steps starting from potassium [¹³C]cyanide. The intermediate chalcone 9 was formed by acylation of the benzylated phloroglucinol 7 with the caffeic acid synthon 6, using the trifluoroacetic mixed anhydride. The flavonoid skeleton was then obtained by previously described reactions such as the reduction of chalcone 9 and dihydroxylation of flavene 11. Such [¹³C]-labelled polyphenols should prove to be useful tools for human biological investigations.

Original language	English
Pages (from-to)	1279-1283
Number of pages	5
Journal	European Journal of Organic Chemistry
Issue number	7
DOIs	https://doi.org/10.1002/1099-0690(200004)2000:7<1279::aid-ejoc1279>3.0.co;2-d
Publication status	Published - 1 Jan 2000
Externally published	Yes

Keywords

Carbon 13
Catechin
Flavonoids
French paradox
Isotopic labelling
Total synthesis

Access to Document

10.1002/1099-0690(200004)2000:7<1279::aid-ejoc1279>3.0.co;2-d

Cite this

@article{4ddbabc164354a5da01528393f45c694,

title = "Total synthesis of isotopically labelled flavonoids, 2: 13C-labelled (±)-catechin from potassium [13C]cyanide",

abstract = "Racemic 4-[13C]catechin 14 has been synthesized in ten steps starting from potassium [13C]cyanide. The intermediate chalcone 9 was formed by acylation of the benzylated phloroglucinol 7 with the caffeic acid synthon 6, using the trifluoroacetic mixed anhydride. The flavonoid skeleton was then obtained by previously described reactions such as the reduction of chalcone 9 and dihydroxylation of flavene 11. Such [13C]-labelled polyphenols should prove to be useful tools for human biological investigations.",

keywords = "Carbon 13, Catechin, Flavonoids, French paradox, Isotopic labelling, Total synthesis",

author = "Bastien Nay and Val{\'e}rie Arnaudinaud and Peyrat, \{Jean Fran{\c c}ois\} and Alain Nuhrich and G{\'e}rard Deffieux and M{\'e}rillon, \{Jean Michel\} and Joseph Vercauteren",

year = "2000",

month = jan,

day = "1",

doi = "10.1002/1099-0690(200004)2000:7<1279::aid-ejoc1279>3.0.co;2-d",

language = "English",

pages = "1279--1283",

journal = "European Journal of Organic Chemistry",

issn = "1434-193X",

number = "7",

}

TY - JOUR

T1 - Total synthesis of isotopically labelled flavonoids, 2

T2 - 13C-labelled (±)-catechin from potassium [13C]cyanide

AU - Nay, Bastien

AU - Arnaudinaud, Valérie

AU - Peyrat, Jean François

AU - Nuhrich, Alain

AU - Deffieux, Gérard

AU - Mérillon, Jean Michel

AU - Vercauteren, Joseph

PY - 2000/1/1

Y1 - 2000/1/1

N2 - Racemic 4-[13C]catechin 14 has been synthesized in ten steps starting from potassium [13C]cyanide. The intermediate chalcone 9 was formed by acylation of the benzylated phloroglucinol 7 with the caffeic acid synthon 6, using the trifluoroacetic mixed anhydride. The flavonoid skeleton was then obtained by previously described reactions such as the reduction of chalcone 9 and dihydroxylation of flavene 11. Such [13C]-labelled polyphenols should prove to be useful tools for human biological investigations.

AB - Racemic 4-[13C]catechin 14 has been synthesized in ten steps starting from potassium [13C]cyanide. The intermediate chalcone 9 was formed by acylation of the benzylated phloroglucinol 7 with the caffeic acid synthon 6, using the trifluoroacetic mixed anhydride. The flavonoid skeleton was then obtained by previously described reactions such as the reduction of chalcone 9 and dihydroxylation of flavene 11. Such [13C]-labelled polyphenols should prove to be useful tools for human biological investigations.

KW - Carbon 13

KW - Catechin

KW - Flavonoids

KW - French paradox

KW - Isotopic labelling

KW - Total synthesis

U2 - 10.1002/1099-0690(200004)2000:7<1279::aid-ejoc1279>3.0.co;2-d

DO - 10.1002/1099-0690(200004)2000:7<1279::aid-ejoc1279>3.0.co;2-d

M3 - Article

AN - SCOPUS:0034107586

SN - 1434-193X

SP - 1279

EP - 1283

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 7