Download PDF
Synfacts 2011(8): 0817-0817  
DOI: 10.1055/s-0030-1260675
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of Buprenorphine

Contributor(s): Philip Kocienski
L. Werner, A. Machara, D. R. Adams, D. P. Cox, T. Hudlicky*
Brock University, St. Catharines, Canada and Noramco, Inc., Wilmington, USA
Further Information

Publication History

Publication Date:
20 July 2011 (online)

    Permissions and Reprints

Significance

Buprenorphine is a semisynthetic opiate that acts as a partial agonist at the µ- and δ-receptors and a competitive antagonist at the κ-receptor. It is used to treat acute pain at low doses, and at higher doses, it is used in combination with naloxone to treat opiate addiction. The small-scale synthesis depicted starts with oripavine and features the N-demethylation of the oripavine quaternary salt C under mild conditions to access the N-cyclopropylmethyl nororipavine E.