65022-58-4

Upstream product

• 64982-82-7 1,2,10,11-tetramethoxy-6-methyl-5,6,7,8,13,14-hexahydrodibenzoazecine-13,14-diol 
• 64982-76-9 2,3,11,12-Tetramethoxy-7-methyl-5,8,13,13a-tetrahydro-6H-isoquino[3,2-a]isoquinolinium; iodide 
• 64982-77-0 2,3,11,12-Tetramethoxy-7-methyl-5,8,13,13a-tetrahydro-6H-isoquino[3,2-a]isoquinolinium; chloride 
• 64982-81-6 trans-1,2,10,11-tetramethoxy-6-methyl-5,6,7,8-tetrahydrodibenzazecine 

Downstream Products

• 14028-91-2 (+/-)-cis-alpinigenine 
• 14028-91-2 (+/-)-alpinigenine 

Relevant academic research and scientific papers

Total Synthesis of the Alkaloids (+/-)-Alpinigenine and (+/-)-cis-Alpinigenine

A stereoselective synthesis of the rhoeadine alkaloid (+/-)-cis-alpinigenine is described.Hofmann elimination of the known tetracyclic base (4) gave the trans-azecine (7) which afforded the diol (13) on oxidation with N-bromosuccinimide.Periodic acid cleavage of (13) yielded the dibenzaldehyde (14), which on photolysis resulted in the formation of (+/-)-cis-alpinigenine (20-30percent) and (+/-)-alpinigenine (1percent) involving endo (16) and exo (15) (4s+2s) intramolecular additions respectively of the intermediate photodienol-E (Scheme 1).