Application of aryl siloxane cross-coupling to the synthesis of allocolchicinoids.
In this communication, we report a new approach to the allocolchicine carbocyclic skeleton based upon an aryl siloxane coupling reaction and a phenanthrol ring expansion. These key steps allow for the selective functionalization of every carbon within the carbocyclic framework. The siloxane coupling-phenanthrol sequence was applied to the synthesis of two allocolchicinoids, including the first fully synthetic approach to N-acetyl colchinol-O-methyl ether (NCME).
Seganish
W Michael
WM
Department of Chemistry and Biochemistry, University of Maryland, College Park, MD 20742, USA.
DeShong
Philip
P
D003078:Colchicine / Q000031:analogs & derivatives* / Q000737:chemistry; D015394:Molecular Structure
C032782:allocolchicine; D003078:Colchicine