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Synfacts 2008(4): 0330-0330
DOI: 10.1055/s-2008-1042882
DOI: 10.1055/s-2008-1042882
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York
Synthesis of NSC 51046
S. Djurdjevic, J. R. Green*
University of Windsor and St. Clair College of Applied Arts and Technology, Windsor, Canada
Further Information
Publication History
Publication Date:
19 March 2008 (online)
Significance
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.