Scheme 8. Synthesis of the oxygenated 3-alkylpyridine marine alkaloid analogue compounds 177 and 178. Reagents and conditions: (a) HBr (aq), toluene, reflux; (b) NaN3, DMSO, r.t., 12 h; (c) MsCl, Et3N, methylene chloride, stirring, 3 h; (d) NaOH, Bu4N+Br−; (e) LiAlH4, THF; (f) methyl acrylate, toluene, reflux; (g) Boc2O, methylene chloride; (h) BnCl, reflux.
