183626-27-9Relevant academic research and scientific papers
Tandem sequence of phenol oxidation and intramolecular addition as a method in building heterocycles
Ratnikov, Maxim O.,Farkas, Linda E.,Doyle, Michael P.
, p. 10294 - 10303 (2013/01/15)
A tandem phenol oxidation-Michael addition furnishing oxo- and -aza-heterocycles has been developed. Dirhodium caprolactamate [Rh 2(cap)4] catalyzed oxidation by T-HYDRO of phenols with alcohols, ketones, amides, carboxylic acids, and N-Boc protected amines tethered to their 4-position afforded 4-(tert-butylperoxy)cyclohexa-2,5-dienones that undergo Bronsted acid catalyzed intramolecular Michael addition in one-pot to produce oxo- and -aza-heterocycles in moderate to good yields. The scope of the developed methodology includes dipeptides Boc-Tyr-Gly-OEt and Boc-Tyr-Phe-Me and provides a pathway for understanding the possible transformations arising from oxidative stress of tyrosine residues. A novel method of selective cleavage of O-O bond in hindered internal peroxide using TiCl4 has been discovered in efforts directed to the construction of cleroindicin F, whose synthesis was completed in 50% yield over just 3 steps from tyrosol using the developed methodology.
From p-benzoquinone to cyclohexane chirons: First asymmetric synthesis of (+)-rengyolone and (+)- and (-)-menisdaurilide
Busque, Felix,Canto, Mariona,De March, Pedro,Figueredo, Marta,Font, Josep,Rodriguez, Sonia
, p. 2021 - 2032 (2007/10/03)
Starting from a common, easily available, enantiopure monoketal of p-benzoquinone, the synthesis of a large number of cyclohexane chirons has been achieved. The first synthesis of (+)-rengyolone and (+)- and (-)-menisdaurilide has been performed from one of these new building blocks. The wide variety of functional groups of this series of chirons makes them useful for subsequent synthetic processes.
First synthesis of (+)-rengyolone and (+)- and (-)-menisdaurilide
Canto, Mariona,De March, Pedro,Figueredo, Marta,Font, Josep,Rodriguez, Sonia,Alvarez-Larena, Angel,Piniella, Juan F.
, p. 455 - 459 (2007/10/03)
The benzofuranone natural products (+)-rengyolone and (+)- and (-)-menisdaurilide have been synthesised for the first time from a common enantiopure cyclohexane building block derived from a monoketal of p-benzoquinone.
