359882-24-9Relevant articles and documents
Synthesis of (-)-aphanorphine using a sulfur-directed aryl radical cyclization
Tamura, Osamu,Yanagimachi, Takehiko,Ishibashi, Hiroyuki
, p. 3033 - 3041 (2007/10/03)
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.