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Synthesis of NSC 51046
S. Djurdjevic, J. R. Green*
University of Windsor and St. Clair College of Applied Arts and Technology, Windsor, Canada
19 March 2008 (online)
NSC 5106 (N-acetylcolchinol methyl ether) is a degradation product of colchicine that arrests cell mitosis by inhibiting tubulin assembly. The synthesis depicted features (1) an efficient Suzuki-Miyaura coupling to generate the biaryl C and (2) an intramolecular Nicholas reaction (E → F) to generate the seven-membered B-ring.