Prenylated phenols

Hoarau, C. Pettus, T. R. R. Strategies for the preparation of differentially protected orlho-prenylated phenols. Synlett 2003, 1, 127-137. 

Fukai, T. and Nomura, T., New NMR structure determination methods for prenylated phenols, Basic Life Sciences, 66 (Plant Polyphenols 2), 259, 1999. 

Togashi M, Masuda H, Kawada T, Tanaka M, Saida K, Ando K, Tamura G, Magae J (2002) PPARy Activation and Adipocyte Differentiation Induced by AS-6, a Prenyl-phenol Antidiabetic Antibiotic. J Antibiot 55 417... 

A combinatorial natural-product-like and diversity-orientated library of 10 000 benzopyran-based small molecules was constructed by Nicolaou and coworkers [74, 75]. They chose a solid-phase approach and an anchoring strategy that does not limit complexity building operations (Scheme 14.11). They used a polystyrene-based selenyl bromide resin (43) on which substrates can be immobilized by electrophilic cyclization reactions. Here, ortho-prenylated phenol 44 was reacted with the selenyl bromide (43) to form the benzopyran scaffold (45) via a 6-endo-trig cyclization. 

One reason that dominant plants are successful in semi-arid and arid ecosystems is due to the high concentration of terpenoids and prenylated phenolics that repel and/or deter feeding by herbivorous insects. Compounds like sesquiterpene lactones and benzopyrans are present in high quantities in the leaves of species of Pjajl t h ij jn, E n c e l i a and D i c o r i a and have been demonstrated to be effective feeding deterrents against known economic insect pests. Ijt vivo experiments are still needed in the field with bioactive constituents to better understand their effects on native phytophagous insects. 

Dibenzonaphthyridinone alkaloids, prenylated phenols, benzoFurans and chromenes... 

Triterpenoid Saponins Phenolic Compounds Recent Methods of Structure Determination of Prenylated Phenols Biological Activities of Phenolic Constituents of Glycyrrhiza Species... 

The farnesylhydroquinone (433) is reminiscent of the prenylated phenols, e.g. cristatic acid (251) and scutigeral (253), produced by species of Albatrellus and discussed in Section 3.1. 

Recent Methods of Structure Determination of Prenylated Phenols. 51... 

There are a number of reports dealing with the phenolic constituents of the aerial parts of Glycyrrhiza species. About thirty new prenylated phenols have been isolated these compounds are not generally found in the underground parts. 

The benzylic methylene carbon signal of the prenyl or E)-3,7-dimethyl-2,6-octadienyl (geranyl) group (Cl) of phenols appears between 8 20-30. In the course of our work on prenylated phenols, we... 

Fukai, T., Q.-H. Wang, and T. Nomura Phenolic Constituents of Glycyrrhiza Species. 6. Six Prenylated Phenols from Glycyrrhiza uralensis. Phytochem., 30, 1245 (1991). 

Fukai T, Wang Q-H, Nomura T (1991) Six prenylated phenols from Glycyrrhiza uralensis. 

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