94535-01-0Relevant articles and documents
Total synthesis of incargranine A
Brown, Patrick D.,Lawrence, Andrew L.
supporting information, p. 1698 - 1702 (2019/02/20)
Synthetic studies into the origins of the alkaloid incargranine A have resulted in the development of a four-step (longest linear sequence) total synthesis. This synthesis has been scaled-up to provide gram-scale quantities of material, which would alternatively require extraction of several metric-tons of dried-whole Chinese Trumpet-Creeper plants (Incarvillea mairei var. grandiflora).
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.
Oxidative de-aromatization of para-alkyl phenols into para-peroxyquinols and para-quinols mediated by oxone as a source of singlet oxygen
Carreno, M. Carmen,Gonzalez-Lopez, Marcos,Urbano, Antonio
, p. 2737 - 2741 (2007/10/03)
(Chemical Equation Presented) Easy does it: Easily handled and environmentally safe oxone generates singlet oxygen which effects the simple and selective oxidative de-aromatization of para-alkyl phenols 1 into para-peroxyquinols 2 under very mild conditions with good to excellent yields. A one-pot access to para-quinols 3 from 1 is also possible after treatment of the crude reaction mixture with sodium thiosulfate.