321835-84-1

Upstream product

• 943-89-5 (E)-3-(4-methoxyphenyl)acrylic acid 
• 151813-62-6 (-)-(S)-8-(4-methoxyphenyl)-1,5,9,13-tetraazacycloheptadecan-6-one 
• 321835-82-9 (-)-(2S)-2-(4-methoxyphenyl)-1,5,9,14-tetraazabicyclo[12.3.1]octadecan-4-one 
• 373360-25-9 (-)-(S)-8-(4-methoxyphenyl)-1,13-bis[(4-methylphenyl)sulfonyl]-1,5,9,13-tetraazacycloheptadecan-6-one 
• 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 
• 321835-85-2 (-)-(S)-3-(4-methoxyphenyl)-N-{3-[(4-methylphenylsulfonyl)amino]propyl}-3-({3-[(4-methylphenylsulfonyl)amino]propyl}amino)propanamide 
• 321835-83-0 (-)-(2S)-9-[(E)-3-(4-methoxyphenyl)prop-2-enoyl]-2-(4-methoxyphenyl)-1,5,9,14-tetraazabicyclo[12.3.1]octadecan-4-one 

Downstream Products

• 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 
• 71461-13-7 (-)-ephedradine A 

Relevant academic research and scientific papers

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.

The asymmetric synthesis of the [D8]-labeled (-)-(S)-dihydroxyverbacine, the terminal precursor in the biogenesis of the macrobicyclic spermine alkaloids aphelandrine and orantine

The asymmetric synthesis of the unlabeled and [D8]-labeled terminal precursors, 4 ((-)-(S)-dihydroxyverbacine) and 19, respectively, in the biogenesis of the spermine alkaloids aphelandrine (5) and orantine (6), respectively, is described. A pa