73465-24-4

Upstream product

• 89044-86-0 N-(4-aminobutyl)-4-phenylazetidin-2-one 
• 73397-38-3 ethyl 3-phenyl-4,9,13-triazatridecanoate 
• 536-74-3 phenylacetylene 
• 2216-94-6 phenylpropynoic acid ethyl ester 
• 5661-55-2 4-phenylazetidin-2-one 
• 76528-86-4 1-(4,5-Dihydro-3H-pyrrol-2-yl)-4-phenyl-azetidin-2-one 
• 73397-37-2 3-[4-(3-Amino-propylamino)-butylamino]-3-phenyl-propionatetetrabutyl-ammonium; 
• 73397-40-7 (Z)-3-Phenyl-3-[4-(tetrahydro-pyrimidin-1-yl)-butylamino]-acrylic acid ethyl ester 
• 73397-41-8 (Z)-3-[4-(3-Amino-propylamino)-butylamino]-3-phenyl-acrylic acid ethyl ester 
• 94-02-0 ethyl 3-oxo-3-phenylpropionate 
• 73453-98-2 1-(4-aminobutyl)-1,2,3,4,5,6-hexahydropyrimidine 
• 124-20-9 N-(3-aminopropyl)-1,4-diaminobutane 
• 79405-59-7 ethyl 11-cyano-4,9-diaza-3-phenyl-2-undecenoate 
• 4748-73-6 N-(cyanoethyl)-1,4-diaminobutane 

Downstream Products

• 79435-40-8 (+/-)-celallocinnine 
• 53938-06-0 Dihydrocelacinnin 
• 79435-39-5 N-acetyl-(+/-)-celacinnine 
• 53938-10-6 3-[Acetyl-(4-{(3-acetylamino-propyl)-[(E)-(3-phenyl-acryloyl)]-amino}-butyl)-amino]-3-phenyl-propionic acid ethyl 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.

A NEW SYNTHESIS OF (+/-)-CELACINNINE BY MEANS OF NON-SPERMIDINE-BASED METHODOLOGY

(+/-)-Celacinnine was synthesized relying on the novel methodology which features nucleophilic ring opening of 2-substituted 5,6-dihydro-4H-1,3-oxazine as a carboxamide synthon and requires neither spermidine nor amino acid condensation process for the la

Total Synthesis of (+/-)-Celacinnine, (+/-)-Celallocinnine, (+/-)-Celafurine, and (+/-)-Celabenzine

The total synthesis of spermidine alkaloids, (+/-)-celacinnine (2), (+/-)-celallocinnine (3), (+/-)-celafurine (4), and (+/-)-celabenzine (5), is described.The use of boron-templated cyclization within the context of constructing macrolactam has been explored, and the combination of triamino ester with tris(dimethylamino)borane is found to be highly efficient.The present cyclization in addition to the refinement of each step produces macrocyclic spermidine alkaloids, 2, 4, and 5, by a five-step sequence in ca. 41percent overall yield starting from 1,4-diaminobutane.Irradiation of 2 affords 3 in 50percent yield.

TRANSAMIDATION REACTIONS IN THE FORMATION OF MACROCYCLIC LACTAMS. A TOTAL SYNTHESIS OF CELLACINNINE.

The macrocyclic spermidine alkaloid, cellacinnine, has been synthetized by methods involving successive ring expansion reactions.One route starts with 4-phenyl-2-azetidinone; another, with piperidazine.

Chemistry of Naturally Occuring Polyamines. 1. Total Synthesis of Celacinnine, Celabenzine, and Maytenine

New methods for the selective functionalization of spermidine and other naturally occurring polyamines have been employed in highly convergent total syntheses of the title compounds.