476312-69-3

Upstream product

• 15463-91-9 3-bromo-3-phenylpropionic acid 
• 68076-36-8 1-amino-4-[(tert-butyloxycarbonyl)amino]butane 

Downstream Products

• 73465-24-4 (+/-)-celacinnine 
• 141991-06-2 1-(3-aminopropyl)-4-phenyl-1,5-diazacyclononan-2-one 
• 76528-88-6 4-phenyl-N-(3-phthalimidopropyl)-1,5-diazacyclononan-2-one 
• 73397-35-0 2-phenyl-1,5,9-triazacyclotridecan-4-one 
• 76528-87-5 4-phenyl-1,5-diazacyclononan-2-one 
• 89044-86-0 N-(4-aminobutyl)-4-phenylazetidin-2-one 

Relevant academic research and scientific papers

β-lactams as building blocks in the synthesis of macrocyclic spermine and spermidine alkaloids

Syntheses of the macrocyclic spermidine alkaloids (±)-celacinnine (1) and (±)-dihydroperiphylline (2) as well as the related spermine alkaloid (±)-verbascenine (3) were accomplished by means of sequential ring expansions of smaller lactam rings. Three ring expansion methods were employed: (1) transamidation of N-(aminoalkyl)lactams, (2) β-lactam-lactim ether condensation followed by reductive cleavage of the bicyclic 4-oxotetrahydropyrimidine product with NaBH3CN/AcOH and (3) bicyclic acyl hydrazine formation followed by N-N bond cleavage with Na/NH3. Each synthesis features ring expansion of a 4-phenylazetidin-2-one intermediate that undergoes transamidative ring expansion or lactim ether condensation.