139006-75-0

Upstream product

• 418755-58-5 6-bromo-7-methoxybenzo[1,3]dioxole-5-carboxylic acid ethyl ester 
• 182163-96-8 3,4,5-trimethoxyphenylboronic Acid 
• 1441119-51-2 (1R,2S)-2-methyl-3-methylene-1-(3',4',5',6-tetramethoxy-4,5-methylenedioxybiphenyl-2-yl)butane-1,4-diol 
• 1441119-49-8 (1R,2S)-2-methyl-1-(3',4',5',6-tetramethoxy-4,5-methylenedioxybiphenyl-2-yl)-3-[(triisopropylsilyloxy)methyl]but-3-en-1-ol 
• 1441119-47-6 (E)-1-[(3',4',5',6-tetramethoxy-4,5-methylenedioxybiphenyl-2-yl)methoxy]-2-(triisopropylsilyloxymethyl)but-2-ene 
• 1441119-45-4 ethyl (3',4',5',6-tetramethoxy-4,5-methylenedioxybiphenyl-2-yl)carboxylate 
• 870094-81-8 [7-methoxy-6-(3,4,5-trimethoxyphenyl)-benzo[1,3]dioxol-5-yl]methanol 

Relevant academic research and scientific papers

Divergent Total Syntheses of Gymnothelignan N, Beilschmin A, and Eupomatilones 1, 3, 4, and 7

A seven-step asymmetric total synthesis of gymnothelignan N is detailed in the current report. The approach is based on an early-stage one-carbon homologative lactonization reaction, which we recently revisited and modified to construct the core γ-butyrolactone motif with the requisite β,γ-vicinal stereogenic centers. By design, the utilization of the same chiral γ-butyrolactone intermediate permitted the rapid and effective divergent assembly of optically active eupomatilones 1, 3, 4, and 7 in five or six steps from commercially available materials. This represents one of the shortest and highest-yielding syntheses reported to date.

Total synthesis of eupomatilones 1, 2, and 5 by enantioselective [2,3]-wittig rearrangement

In this study, the asymmetric total synthesis of eupomatilones 1, 2, and 5 has been accomplished. These compounds are lignan congeners containing a biaryl system bearing an α-methylene γ-lactone. They were isolated from the Australian shrub Eupomatia benn