jo200567n_si_001.pdf (1.98 MB)
Synthesis of Buprenorphine from Oripavine via N-Demethylation of Oripavine Quaternary Salts
journal contribution
posted on 2011-06-03, 00:00 authored by Lukas Werner, Ales Machara, David R. Adams, D. Phillip Cox, Tomas HudlickyBuprenorphine was synthesized from oripavine by a sequence involving the conversion of oripavine into its cyclopropylmethyl quaternary salt, N-demethylation with thiolate to N-cyclopropylmethyl nororipavine, and conversion of this material to the title compound by previously available methods. The new synthesis avoids toxic reagents used previously, is shorter, and proceeds in comparable yields. Experimental and spectral data are provided for all new compounds.