107534-93-0Relevant articles and documents
Synthesis of Lignans Based on a Borate-mediated One-pot Sequential Suzuki-Miyaura Coupling of Cyclic Boranes
Sato, Ko,Tanaka, Hiroshi
supporting information, p. 9422 - 9428 (2021/05/26)
Lignans are a group of polyphenolic phytochemicals that possess a large spectrum of chemical structures and biological activities. Here the syntheses of lignans – anwulignan, burseran, dehydroxycubebin, ruburisandrin B, and sesamin – are achieved based on a borate-mediated one-pot sequential Suzuki-Miyaura coupling of cis- and trans-fused bicyclic boranes, which were prepared by diastereoselective cyclic hydroboration of exo-cyclic diene with cyclopentyl- and thexylboranes, respectively. A one-pot sequential Suzuki-Miyaura coupling of each cyclic borate with various aryl bromides initiated by activation of the cyclic borane with the carbon nucleophile provided 2,3-dibenzylbutane derivatives with different aromatic substituents. Finally, the syntheses of naturally occurring lignans were accomplished in several steps from the products of Suzuki-Miyaura coupling.
Regioselective Cleavage of the Methylenedioxy Group: Conversion of (-)-Austrobailignan-5 to (-)-Dihydroguaiaretic Acid
Rao, Koppaka V.,Chattopadhyay, Sunil K.
, p. 1427 - 1429 (2007/10/02)
A method for the selective cleavage of a benzodioxole (methylenedioxy group) to a methoxyphenol through the use of a p-methylthiophenoxide ion is described.When the procedure was applied to a lignan derivative such as (-)-austrobailignan-5, the reaction w
The structure of chicanine, a new lignan from Schisandra sp.
Liu, Jia-Sen,Huang, Mei-Fen,Gao, Yao-Liang,Findlay, John A.
, p. 1680 - 1684 (2007/10/02)
A new lignan, chicanine, isolated from the fruit of Schisandra sp., is shown to possess structure 1, 2S-(3-methoxy-4-hydroxyphenyl)-3R,4S-dimethyl-5S-(3,4-methylenedioxyphenyl)tetrahydrofuran, from spectra analysis and chemical conversions.The tetrahydrof
