182072-32-8

Upstream product

• 181475-12-7 (R)-Benzo[1,3]dioxol-5-yl-[((4S,5S)-2,2-dimethyl-4-phenyl-[1,3]dioxan-5-yl)-methyl-amino]-((R)-5-oxo-tetrahydro-furan-3-yl)-acetonitrile 
• 86-81-7 3,4,5-trimethoxy-benzaldehyde 

Downstream Products

• 445389-57-1 (1R,2S,3S,4R)-1-(1,3-benzodioxol-5-yl)-2,3-di(hydroxymethyl)-4-(3,4,5-trimethoxyphenyl)butan-1,4-diol 
• 445389-55-9 (3R,4S)-4-[(R)-1-(1,3-benzodioxol-5-yl)-1-hydroxymethyl]-3-[(R)-1-hydroxy-1-(3,4,5-trimethoxyphenyl)methyl]tetrahydro-2-furanone 

Relevant academic research and scientific papers

A general approach to the asymmetric synthesis of lignans: (-)-methyl piperitol, (-)-sesamin, (-)-aschantin, (+)-yatein, (+)-dihydroclusin, (+)-burseran, and (-)-isostegane

A highly efficient, diastereo- and enantioselective route was developed to access a great variety of lignans. The asymmetric synthesis of the 2,3-disubstituted γ-butyrolactones 9a-c could be improved in the case of aldol reactions by employing 2.2 equivalents of LiCl as an additive to provide, after purification, highly diastereo- and enantioenriched starting materials for the synthesis of the furofuran lignans (-)-methyl piperitol, (-)-sesamin, and (-)-aschantin. Furthermore, the γ-butyrolactone 15 was converted into dibenzylbutyrolactone lignan (+)-yatein, the dibenzylbutandiol type (+)-dihydroclusin, the tetrahydrofuran type (+)-burseran, and the dibenzocyclooctadiene type (-)-isostegane.