254975-89-8

Upstream product

• 67-56-1 methanol 
• 254975-88-7 (4R)-(-)-3-{[(2R,3R)-5-Bromo-2-(3,4-dimethoxyphenyl)-2,3-dihydrobenzofuran-3-yl]carbonyl}-4-isopropyloxazolidin-2-one 
• 254975-87-6 (4R)-(+)-3-{(2R,3R)-2-[2-(Benzyloxy)-5-bromophenyl]-3-(3,4-dimethoxyphenyl)-3-hydroxypropanoyl}-4-isopropyloxazolidin-2-one 
• 254975-86-5 (R)-(-)-3-[2-(Benzyloxy)-5-bromophenylacetyl]-4-isopropyloxazolidin-2-one 
• 149428-97-7 2-(Benzyloxy)-5-bromophenylacetic acid 
• 120-14-9 3,4-dimethoxy-benzaldehyde 

Downstream Products

• 254975-90-1 (-)-Methyl (2R,3R)-5-[2-(tert-butoxycarbonyl)vinyl]-2-(3,4-dimethoxyphenyl)-2,3-dihydrobenzofuran-3-carboxylate 
• 254975-91-2 (2R,3R)-(-)-5-[2-(tert-Butoxycarbonyl)vinyl]-2-(3,4-dimethoxyphenyl)-2,3-dihydrobenzofuran-3-carboxylic acid 
• 254975-92-3 (2R,3R)-(-)-5-{(1S)-1-[(1R)-N-Benzyl-1-phenylethylamino]-2-(tert-butoxycarbonyl)ethyl}-2-(3,4-dimethoxyphenyl)-2,3-dihydrobenzofuran-3-carboxylic acid 

Relevant academic research and scientific papers

Asymmetric synthesis of the northern segment of ephedradine C

An asymmetric synthesis of the dihydrobenzofuran segment of ephedradine C has been achieved. Key steps include a chiral oxazolidinone-mediated aldol reaction to form a β-hydroxy ester, followed by a novel debenzylation and concomitant intramolecular cyclisation with iodotrimethylsilane. An asymmetric Michael reaction with a homochiral lithium amide was used to form the third and final chiral centre. The absolute stereochemistry of these three centres was confirmed by X-ray crystal-structure determinations.