McGowan G1, Thomas EJ.
Org Biomol Chem. 2009 Jun 21;7(12):2576-90. doi: 10.1039/b903256h. Epub 2009 Apr 27.The combination of a [2,3]-Wittig rearrangement of a suitably substituted cyclohexenylmethyl propargyl ether with a subsequent conversion of the alkyne to a trisubstituted alkene and cyclisation via intramolecular sulfone alkylation has proved to be a useful stereoselective approach to advanced macrocyclic intermediates for a projected synthesis of phomactins. Thus Luche reduction of methyl (1RS,6SR)-2-(bromomethyl)-1,6-dimethyl-4-oxocyclohex-2-ene-1-carboxylate 24 gave methyl (1RS,4RS,6SR)-2-bromomethyl-4-hydroxy-1,6-dimethylcyclohex-2-ene-1-carboxylate 26 which was protected as its (2-trimethylsilylethoxy)methyl ether 27. Read More