Galloyl syntheses

Figure 4. Chemical synthesis of galloyl coenzyme A thioester (4). (1) 4-0-/3-D-glucosidogallic acid (2) AT-succinimidyl 4-0-/3 -D-glucosidogallate (3)...

Tuckmantel, W., Kozikowski, A.P., and Romanczyk, L.J. Jr., Studies in polyphenol chemistry and bioactivity. 1. Preparation of building blocks from (+)-catechin. Procyanidin formation. Synthesis of the cancer cell growth inhibitor, 3-0-galloyl-(2R,3R)-epicatechin-4(3,8-[3,0-galloyl-(2R,3R)-epicatechin], J. Am. Chem. Soc., 121, 12073, 1999. 

Scheme 41. Application of the lead(IV)-mediated oxidative coupling of galloyl phenols to the synthesis of coriariin A.

Scheme 17 Synthesis of epicatechin-(4a 8)-epicatechin (114) and its mono-O-gaiiate (115). Reagents and conditions (a)dry THF, -78 °C (b) n-BusSnH, CF3CO2H (c)48% HF, CH3CN (d) 20% Pd(OH)2/C, H2, EtOAc/MeOH (e) galloylation.

GROSS, S.R. 1982. Synthesis of galloyl coenzyme A thiol ester. Z. Naturforsch. 37C 778-783. 

GROSS, S.R. 1983. Synthesis of mono-, di- and tri-galloyl-3 D glucogallin dependent galloyl transferases from oak leaves. Z. Naturforsch. 

The shikimate pathway is also important in the formation of other molecules such as gallic acid [92] that is essential for the synthesis of galloylated PAs, which are the major PAs found in numerous plants, for instance, in tea (Camellia sinensis) and grapes (Vitis vinifera) [93, 94]. Nevertheless, the galloylation mechanism in PAs remains unknown. 

Glucogallin obtained from the Chinese rhubarb by Gilson has been identified (100) through synthesis as l-0-galloyl-j3-D-glucose. 

Acylglycines. Several acylglycines (acetyl, benzoyi, phenylacetyl, galloyl, etc.) have been used in the azlactone synthesis. Of these, ben-zoylglycine and acetylglycine have been studied most. Each has certain... 

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