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Synfacts 2008(4): 0330-0330  
DOI: 10.1055/s-2008-1042882
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Synthesis of NSC 51046

Contributor(s): Philip Kocienski
S. Djurdjevic, J. R. Green*
University of Windsor and St. Clair College of Applied Arts and Technology, Windsor, Canada
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Publikationsdatum:
19. März 2008 (online)

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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.