99897-28-6

Upstream product

• 58489-52-4 N-methyl-3-(3,4-dimethoxyphenyl)succinimide 
• 99897-25-3 N-methyl-3-(3,4-dimethoxyphenyl)-3-<3-(trimethylsilylmethyl)but-3-en-1-yl>succinimide 
• 99897-26-4 1-methyl-4-(3,4-dimethoxyphenyl)-4-<3-(trimethylsilylmethyl)but-3-en-1-yl>-5-hydroxy-2-pyrrolidone 

Downstream Products

• 6023-73-0 mesembrine 
• 21104-34-7 N-methyl-3a-<3,4-(dimethoxy)phenyl>-2,3,3a,4,5,6,7,7a-octahydroindole-2,6-dione 

Relevant academic research and scientific papers

A new synthesis of (±)-mesembrine involving the intramolecular nucleophilic attack of an allyl anion on a carbonyl function of an imide

A synthesis of (±)-mesembrine by the fluoride ion induced intramolecular cyclization of a suitably substituted allylsilane an to a neighbouring carbonyl function of an imide is described.

INTRAMOLECULAR CYCLIZATION OF ALLYLSILYL SUBSTITUTED N-ACYLIMINIUM IONS. ACCESS TO 1- AND 2-AZABICYCLOALKANES. TOTAL SYNTHESIS OF (+/-)-MESEMBRINE

Access to 1- and 2-azabicycloalkanes by intramolecular cyclization of allylsilanes on α-acyliminium ions is described.This methodology is also used to achieve a highly stereoselective total synthesis of (+/-)-mesembrine.

CYCLISATION OF ALLYL SILANES. FORMAL TOTAL SYNTHESIS OF (+/-)-MESEMBRINE

The intramolecular reaction of an α-acyl iminium ion with an allyl silane occurs under non acidic conditions to afford the key intermediate 8 for the synthesis of (+/-)-mesembrine 1 in a stereospecific manner.