Tuning the Lewis acid phenol \(\varvec{ortho}\) -prenylation as a molecular di
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- 作者：Sebastián N. Jäger ; Exequiel O. J. Porta ; Guillermo R. Labadie
- 关键词：Prenylated natural products ; Phenols ; Friedel–Crafts alkylation ; Selective C ; prenylation
- 刊名：Molecular Diversity
- 出版年：2016
- 出版时间：May 2016
- 年：2016
- 卷：20
- 期：2
- 页码：407-419
- 全文大小：1,090 KB
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Exequiel O. J. Porta (1)
Guillermo R. Labadie (1)
1. Instituto de Química Rosario (IQUIR-CONICET), Facultad de Ciencias Bioquímicas y Farmacéuticas, Universidad Nacional de Rosario, Suipacha 531, S2002LRK, Rosario, Argentina - 刊物类别：Chemistry and Materials Science
- 刊物主题：Chemistry
Analytical Chemistry
Polymer Sciences
Organic Chemistry
Pharmacy - 出版者：Springer Netherlands
- ISSN：1573-501X
文摘
A diversity-oriented approach for the synthesis of various structurally different prenylated alcohols from readily accessible and common precursors was developed. With varying approaches, this article describes some successful examples of a Friedel–Crafts alkylation using methoxyphenols and different prenyl alcohols (geraniol and (E,E)-farnesol). We demonstrated that just by 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 unique products were obtained with good isolated yields by direct alkylation with or without a consecutive \(\pi \)-cationic cyclization.