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Synfacts 2010(10): 1107-1107  
DOI: 10.1055/s-0030-1258068
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of (±)-Bremazocine

Contributor(s): Philip Kocienski
J.-i. Matsuo*, R. Okada, H. Ishibashi
Kanazawa University, Japan
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Publikationsdatum:
22. September 2010 (online)

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Significance

(-)-Bremazocine is a potent κ-­opioid agonist. A synthesis of rac-bremazocine summarized here incorporates the construction of the dihydro-4-pyridone E via the reaction of the 3-ethoxycyclobutanone A with the aldimine B in the presence of titanium tetrachloride. Eighteen examples of the reaction are described.