73366-01-5Relevant articles and documents
Bioinspired total synthesis of tetrahydrofuran lignans by tandem nucleophilic addition/redox isomerization/oxidative coupling and cycloetherification reactions as key steps
Jagtap, Pratap R.,Císa?ová, Ivana,Jahn, Ullrich
supporting information, p. 750 - 755 (2018/02/09)
A very short three-step approach to trans,trans,trans-2,5-diaryl-3,4-dimethyltetrahydrofuran lignans is reported. The carbon skeleton is assembled in a single step based on an unprecedented tandem reaction consisting of 1,2-addition of aryllithium reagents to α,β-unsaturated aldehydes, ruthenium-catalyzed redox isomerization of the resulting alkoxides to enolates and their dimerization triggered by single electron oxidation. The resulting 2,3-dialkyl-1,4-diketones form with moderate to good d/l-diastereoselectivity and are transformed to the target tetrahydrofuran lignans by reduction and diastereoselective cycloetherification.
Total synthesis of cyclogalgravin and its dicarboxyl analog using sc(otf)3-mediated highly diastereoselective ring expansion of 1-(arylhydroxymethyl)cyclopropanecarboxylates
Sakuma, Daichi,Ito, Junki,Sakai, Ryo,Taguchi, Ryota,Nishii, Yoshinori
, p. 610 - 611 (2014/05/20)
The total synthesis of cyclogalgravin and its dicarboxyl analog was achieved by using the SmI2-promoted Reformatsky type reaction and Sc(OTf)3-mediated diastereoselective ring expansion as key steps.
Synthesis of magnoshinin and cyclogalgravin: Modified stobbe condensation reaction
Yvon,Datta,Le,Charlton
, p. 1556 - 1560 (2007/10/03)
The development of new methods for lignan synthesis is reported. A recently reported method for the preparation of 1-aryl-1,2-dihydronaphthalenes is exploited to prepare magnoshinin, a naturally occurring lignan, and cyclogalgravin (3,4-dehydrogalbulin), a derivative of a natural lignan.