57675-12-4

Upstream product

• 131653-21-9 tanegoside B 
• 131653-21-9 (7S,8R,7'S,8'S)-4,9,4',7'-tetrahydroxy-3,3'-dimethoxy-7,9'-epoxylignan 7'-O-β-D-glucopyranoside 
• 928665-77-4 C₂₂H₃₈O₄Si₂ 
• 1135-24-6 3-(4-hydroxy-3-methoxyphenyl)acrylic acid 
• 154083-37-1 4-t-butyldimethylsilyloxy-3-methoxycinnamicacid 

Downstream Products

• 57759-55-4 (2R,3R)-2,3-bis[(4-hydroxy-3-methoxyphenyl)methyl]-1,4-butanediol 

Relevant academic research and scientific papers

A bio-inspired total synthesis of tetrahydrofuran lignans

Lignan natural products comprise a broad spectrum of biologically active secondary metabolites. Their structural diversity belies a common biosynthesis, which involves regioand chemoselective oxidative coupling of propenyl phenols. Attempts to replicate this oxidative coupling have revealed significant challenges for controlling selectivity, and these challenges have thus far prevented the development of a unified biomimetic route to compounds of the lignan family. A practical solution is presented that hinges on oxidative ring opening of a diarylcyclobutane to intercept a putative biosynthetic intermediate. The effectiveness of this approach is demonstrated by the first total synthesis of tanegool in 4 steps starting from ferulic acid, as well as a concise synthesis of the prototypical furanolignan pinoresinol.

Tanegosides A, B, and C, Lignan Glycosides from Trachelospermum liukiuense

Three new tetrahydrofuranosid-lignan glycosides, tanegosides A, B, and C, were isolated from Trachelospermum liukiuense HATSUSIMA, along with 8 lignan glycosides already known in T. asiaticum, and the structures were elucidated by spectral and chemical methods.