321835-85-2

Upstream product

• 98-59-9 p-toluenesulfonyl chloride 
• 444119-35-1 (-)-(S)-N-(3-aminopropyl)-3-({3-[(4-methylphenylsulfonyl)amino]propyl}amino)-(4-methoxyphenyl)propanamide 
• 360059-20-7 (S)-3-Amino-3-(4-methoxy-phenyl)-propionic acid ethyl ester 
• 444119-33-9 methyl (-)-(S)-3-(4-methoxyphenyl)-3-({3-[(4-methylphenylsulfonyl)amino]propyl}amino)propanoate 
• 444119-31-7 4-methyl-N-{3-[(methylsulfonyl)oxy]propyl}benzenesulfonamide 
• 13379-98-1 3-[N-(4-methylphenylsulfonyl)amino]propan-1-ol 
• 131791-82-7 3-amino-3-(4-methoxyphenyl)propionic acid methyl ester 

Downstream Products

• 373360-25-9 (-)-(S)-8-(4-methoxyphenyl)-1,13-bis[(4-methylphenyl)sulfonyl]-1,5,9,13-tetraazacycloheptadecan-6-one 
• 151813-62-6 (-)-(S)-8-(4-methoxyphenyl)-1,5,9,13-tetraazacycloheptadecan-6-one 
• 71461-13-7 (-)-ephedradine A 
• 321835-84-1 (-)-(8S)-1-[(E)-3-(4-methoxyphenyl)prop-2-enoyl]-8-(4-methoxyphenyl)-1,5,9,13-tetraazacycloheptadecan-6-one 
• 312908-82-0 (-)-(8S)-1-[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]-8-(4-hydroxyphenyl)-1,5,9,13-tetraazacycloheptadecan-6-one 
• 69721-57-9 (11S,17S,18S)-aphelandrine 
• 321835-86-3 (-)-(8S)-8-(4-methoxyphenyl)-1,13-(4-tolylsulfonyl)[14,14,15,15,16,16,17,17-2H₈]-1,5,9,13-tetraazacycloheptadecan-6-one 

Relevant academic research and scientific papers

Asymmetric syntheses of the macrocyclic spermine alkaloids (-)-(S)-protoverbine, (-)-(S)-buchnerine, and their naturally occurring congenial alkaloids

Asymmetric syntheses of the following 17-membered macrocyclic spermine alkaloids are presented: (-)-(S)-protoverbine (= (8S)-8-phenyl-1,5,9,13-tetraazacycloheptadecane-6-one: 1), (+)-(S)-protomethine (=(2S)-2-phenyl-1,5,9,14-tetraazabicyclo[12.3.1]octadec

Biomimetic formation of macrocyclic spermine alkaloids

Dihydroxyverbacine (10), a precursor for oxidative phenol coupling, was obtained via (±)-buchnerine (14), whose synthesis is described. The oxidizing system hemin (ferriprotoporphyrin IX chloride)/H2O2 promoted intramolecular coupling of 10 to give the alkaloids aphelandrine (1), orantine (2), and chaenorpine (7). The alkaloids were identified by on-line coupled HPLC and atmospheric-pressure chemical-ionization (APCI) mass spectrometry.