87499-89-6

Upstream product

• 84877-95-2 4-Oxo-[1,5]diazonane-1-carboxylic acid tert-butyl ester 
• 84927-09-3 4-oxo-1,5,9-triazacyclotridecan-1,9-dicarboxylic acid 1-tert-butyl ester 9-(2,2,2-trichloroethyl)ester 
• 87499-90-9 (E)-4-Ethoxy-1,5,9-triaza-cyclotridec-4-ene-1,9-dicarboxylic acid 1-tert-butyl ester 9-(2,2,2-trichloro-ethyl) ester 
• 84877-90-7 (E)-4-Methoxy-1,5,9-triaza-cyclotridec-4-ene-1,9-dicarboxylic acid 1-tert-butyl ester 9-(2,2,2-trichloro-ethyl) ester 
• 87499-88-5 4-oxo-2-phenyl-3,4,6,7,9,10,11,12,14,15-decahydro-2H,5H-1,4a,8,13-tetraazabenzocyclotridecene-8,13-dicarboxylic acid 13-tert-butyl ester 8-(2,2,2-trichloroethyl) ester 
• 84877-90-7 4-methoxy-1,5,9-triazacyclotridec-4-ene-1,9-dicarboxylic acid 1-tert-butyl ester 9-(2,2,2-trichloroethyl) ester 
• 87499-90-9 4-ethoxy-1,5,9-triazacyclotridec-4-ene-1,9-dicarboxylic acid 1-tert-butyl ester 9-(2,2,2-trichloroethyl) ester 
• 84877-96-3 5-[3-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-propyl]-4-oxo-[1,5]diazonane-1-carboxylic acid tert-butyl ester 
• 84877-97-4 5-(3-Amino-propyl)-4-oxo-[1,5]diazonane-1-carboxylic acid tert-butyl ester 
• 84877-98-5 4-oxo-1,5,9-triazacyclotridecane-1-carboxylic acid tert-butyl ester 
• 76405-01-1 7-oxo-1,6-diazabicyclo<4.3.0>nonane 
• 76405-02-2 [1,5]Diazonan-2-one 
• 5661-55-2 4-phenylazetidin-2-one 
• 75-36-5 acetyl chloride 

Downstream Products

• 87499-87-4 13-Acetyl-8-phenyl-1,5,9,13-tetraaza-cycloheptadecan-6-one 
• 87510-19-8 13-acetyl-6-oxo-8-phenyl-1,5,9,13-tetraazcycloheptadecane-1-carboxylic acid 2,2,2-trichloroethyl ester 

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.

NEW APPROACHES TO THE SYNTHESIS OF SPERMINE AND SPERMIDINE ALKALOIDS

New approaches to the formation of macrocyclic lactams are described involving successive ring expansion of 8-lactams and other heterocyclic systems.These methods have been used in the synthesis of a number of spermine and spermidine alkaloids including homaline, celacinnine, dihydroperiphylline, chaenorhine and verbascenine.