Tuning the Lewis Acid Phenol ortho-Prenylation as a Molecular Diversity Tool.

SEBASTIÁN N. JÄGER; EXEQUIEL O. J. PORTA; GUILLERMO R. LABADIE

MOLECULAR DIVERSITY

SPRINGER

Lugar: Berlin; Año: 2016 vol. 20 p. 407 - 419

1381-1991

One of the most fascinating challenges in modern organic chemistry is the design of strategies capable of providing structurally diverse and complex molecules. A diversity-oriented approach for the synthesis of various structurally different molecules from readily accessible and common precursors was developed. This article describes different approaches, highlighting some successful examples of a Friedel-Crafts alkylation using methoxyphenols and different prenyl alcohols (geraniol and farnesol). We demonstrated that just varying the stoichiometry of the Lewis acid used the course of the reaction can be shifted to produce the alkylated or the cyclized product. Eighteen different new products were obtained with good isolated yields by direct alkylation with or without a consecutive - cationic cyclization.