115262-34-5

Upstream product

• 104331-18-2 ethyl 4-oxocyclohex-2-enecarboxylate 
• 115262-32-3 (4aS*,9bR*)-ethyl 6-methoxy-3-oxo-1,2,3,4,4a,9b-hexahydrodibenzofuran-9b-carboxylate ethylene acetal 
• 115262-31-2 C₁₇H₂₀O₆ 
• 115262-26-5 (4aS*,9bR*)-ethyl 6-methoxy-3-oxo-1,2,3,4,4a,9b-hexahydrodibenzofuran-9b-carboxylate 
• 115262-27-6 (4aS*,9bR*)-ethyl 6-hydroxy-3-oxy-1,2,3,4,4a,9b-hexahydrodibenzofuran-9b-carboxylate 
• 104380-32-7 2,3-dimethoxyphenyl-lead triacetate 
• 104331-23-9 ethyl 1-(2,3-dimethoxyphenyl)-4-oxocyclohex-2-enecarboxylate 
• 115262-33-4 (4aS*,9bR*)-9b-hydroxymethyl-6-methoxy-3-oxo-1,4,4a,9b-tetrahydrodibenzofuran-3(2H)-one ethylene acetal 
• 98-59-9 p-toluenesulfonyl chloride 

Relevant academic research and scientific papers

Use of the Electrophilic Arylation Reaction of Aryl-lead Triacetates in a Sythesis of (+/-)-Lycoramine

A formal total synthesis of (+/-)-lycoramine is reported.The quaternary carbon centre of the alkaloid was produced by a novel electrophilic arylation of the mixture of isomeric vinylogous keto esters (4) and (5) by 2,3-dimethoxyphenyl-lead triacetate.The resulting key intermediate (7c), which was formed in almost quantitative yield, was converted in a straightforward sequence into the formamide (25), from which the alkaloid has been produced previously by a Bischler-Napieralski cyclisation.Functional group protection was only required at one stage in the synthesis.