72730-18-8

Upstream product

• 5658-50-4 1-(3,4,5-trimethoxyphenyl)propan-1-one 
• 29652-81-1 1-(3,4,5-trimethoxyphenyl)-1-propanol 
• 2675-79-8 1-bromo-3,4,5-trimethoxybenzene 
• 594-19-4 tert.-butyl lithium 
• 107-02-8 acrolein 
• 86-81-7 3,4,5-trimethoxy-benzaldehyde 
• 52190-29-1 2-bromo-1-(3,4,5-trimethoxyphenyl)propan-1-one 

Downstream Products

• 14335-63-8 (1α,2β,3β)-6,7,8-trimethoxy-2,3-dimethyl-1-(3,4,5-trimethoxyphenyl)-1,2,3,4-tetrahydronaphthalene 

Relevant academic research and scientific papers

Bioinspired total synthesis of tetrahydrofuran lignans by tandem nucleophilic addition/redox isomerization/oxidative coupling and cycloetherification reactions as key steps

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.