Synthesis of the azaphilones using copper-mediated enantioselective oxidative dearomatization.
نویسندگان
چکیده
An approach to the asymmetric synthesis of the azaphilone natural products is reported involving copper-mediated enantioselective oxidative dearomatization of o-alkynylbenzaldehydes. The approach was successfully applied to the synthesis of (-)-S-15183a and several unnatural azaphilones.
منابع مشابه
An enantioselective organocatalytic oxidative dearomatization strategy.
The inherent reactivity and functionality stored within aromatic systems provide numerous possibilities for the synthesis of 3-D organic structures via dearomatization processes.1,2 Under oxidizing conditions, the dearomatization of orthoand para-substituted phenols forms cyclohexadienones,3 and these products have found widespread use in the chemical synthesis of natural products.4 Additionall...
متن کاملSynthesis of 3-alkyl spiro[4,5]trienones by copper-catalyzed oxidative ipso-annulation of activated alkynes with unactivated alkanes.
A Cu-catalyzed oxidative ipso-annulation of activated alkynes with unactivated alkanes for the synthesis of 3-alkyl spiro[4,5]trienones is described. This method allows the formation of two carbon-carbon bonds and one carbon-oxygen bond in a single reaction through a sequence of C-H oxidative coupling, ipso-carbocyclization and dearomatization.
متن کاملEnantioselective dearomatization of isoquinolines by anion-binding catalysis en route to cyclic α-aminophosphonates.
An enantioselective dearomatization of isoquinolines has been developed using chiral anion-binding catalysis. This transformation, catalyzed by a simple and easy to prepare tert-leucine-based thiourea derivative, makes use of silyl phosphite as a nucleophile and generates cyclic α-aminophosphonates. This is the first time asymmetric anion-binding catalysis has been applied to the synthesis of α...
متن کاملChiral aryl iodide catalysts for the enantioselective synthesis of para-quinols.
Molecular modelling of an iodine(III) phenoxide was used as a starting point in the design of chiral aryl iodide catalysts for stereoselective oxidative dearomatization reactions. Using this approach, catalysts derived from 8-iodotetralone and tartaric acid were constructed and used to synthesize enantioenriched para-quinols from phenols.
متن کاملCatalytic asymmetric hydroxylative dearomatization of 2-naphthols: synthesis of lacinilene derivatives.
An enantioselective hydroxylative dearomatization of 2-naphthols with oxaziridines has been accomplished using a N,N'-dioxide-scandium(iii) complex catalyst. Various substituted ortho-quinols could be obtained in high yields (up to 99%) and enantioselectivities (up to 95 : 5 er). This methodology could be applied in the synthesis of bioactive lacinilenes in a gram-scale reaction. Based on the e...
متن کاملذخیره در منابع من
با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید
عنوان ژورنال:
- Journal of the American Chemical Society
دوره 127 26 شماره
صفحات -
تاریخ انتشار 2005