1201329-87-4Relevant academic research and scientific papers
Lewis acid-catalyzed enantiospecific [3 + 2] annulations of γ-butyrolactone fused cyclopropanes with aromatic aldehydes: Synthesis of chiral furanolignans
Shen, Yue,Yang, Peng-Fei,Yang, Gaosheng,Chen, Wen-Long,Chai, Zhuo
, p. 2688 - 2696 (2018/04/30)
An enantiospecific [3 + 2] annulation of γ-butyrolactone fused cyclopropanes with aromatic aldehydes was realized under Lewis acid catalysis. This method provides facile access to a series of chiral furanolignan derivatives bearing multiple contiguous stereogenic centers in good-to-excellent yields, exclusive diastereoselectivities and excellent enantiopurities under mild reaction conditions. Elaboration work on the product of this reaction delivers stereoisomeric analogues of (+)-virgatusin and suggests a structural revision might be necessary for a previously reported isolated natural product.
Syntheses and antimicrobial activity of tetrasubstituted tetrahydrofuran lignan stereoisomers
Nakato, Tomofumi,Yamauchi, Satoshi,Tago, Ryosuke,Akiyama, Koichi,Maruyama, Masafumi,Sugahara, Takuya,Kishida, Taro,Koba, Yojiro
experimental part, p. 1608 - 1617 (2010/03/01)
The syntheses of all stereoisomers of tetrasubstituted tetrahydrofuran lignan were accomplished, and the antimicrobial activity was examined. The 9, 9′-diol compound bearing (7R, 7′R, 8R, 8′R) and (7R, 7′S, 8R, 8′R) stereochemistry showed the strongest antibacterial activity against Listeria denitrificans and Bacillus subtilis, respectively. It was also found that ()-virgatusin bearing (7S, 7′R, 8S, 8′S) stereochemistry had strongest antifungal activity.
