DIRECT C-11 FUNCTIONALISATION OF ANATOXIN-A. APPLICATION TO THE SYNTHESIS OF NEW LIGAND-BASED STRUCTURAL PROBES
1997
A variety of methods have been evaluated for the
functionalisation of
the C-11 methyl group of anatoxin-a. Reaction of N-Boc
anatoxin-a 9 with PhI(OH)OTs (Koser’s reagent) represents the
method of choice and gives the synthetically versatile
α-tosyloxy ketone 10. This intermediate provides a
convenient vehicle for the attachment of spacer units to C-11
via a thioether linkage which has been applied to the synthesis
of the dansylated [N-(5-dimethylamino-1-naphthylsulfonyl)]
anatoxin-a derivatives. Preliminary biological data relating to the
α-thiomethyl anatoxin-a derivative 16 and the dansylated
ligands, 25 and 26, are also reported.
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