359882-24-9

Upstream product

• 359882-23-8 (2R,4R)-1-benzyloxycarbonyl-2-[(2-bromo-4-methoxyphenyl)methyl]-4-hydroxy-2-(methoxycarbonyl)pyrrolidine 

Downstream Products

• 118964-06-0 (-)-aphanorphine 
• 128524-63-0 (+)-8-O-methylaphanorphine 
• 359882-21-6 (1S,4R)-3-benzyloxycarbonyl-8-methoxy-1-phenylthiomethyl-2,3,4,5-tetrahydro-1,4-methano-3-benzazepine 
• 359882-20-5 (1S,9R)-4-Methoxy-1-phenylsulfanylmethyl-10-aza-tricyclo[7.2.1.0^2,7]dodeca-2⁽⁷⁾,3,5-triene-9,10-dicarboxylic acid 10-benzyl ester 
• 359882-26-1 (1S,4R)-3-benzyloxycarbonyl-8-methoxy-4-methoxycarbonyl-1-phenylthiomethyl-2,3,4,5-tetrahydro-1,4-methano-3-benzazepine 
• 359882-25-0 (S)-1-benzyloxycarbonyl-2-[(2-bromo-4-methoxyphenyl)methyl]-2-methoxycarbonyl-4-(phenylthiomethylene)pyrrolidine 

Relevant academic research and scientific papers

Synthesis of (-)-aphanorphine using a sulfur-directed aryl radical cyclization

Treatment of radical precursor 15a having a vinyl sulfide moiety with Bu3SnH in the presence of AIBN in boiling benzene afforded exclusively the 6-exo cyclization product 16a, whereas similar treatment of the exo-methylene compound 15b gave a mixture of the 6-exo cyclization product 16b and the endo-olefin product 17 formed by a 1,5-hydrogen shift. Based on these findings, the synthesis of (-)-aphanorphine was achieved using a sulfur-directed 6-exo-selective aryl radical cyclization of 22.

Synthesis of (-)-aphanorphine using aryl radical cyclization.

[structure: see text] The synthesis of (-)-aphanorphine was achieved by using Bu(3)SnH-mediated aryl radical cyclization of 1-benzyloxycarbonyl-2-(2-bromo-4-methoxyphenylmethyl)-2-methoxycarbonyl-4-(phenylthiomethylene)pyrrolidine, leading to exclusive fo