Feldman Ken S, Fodor Matthew D
Department of Chemistry, The Pennsylvania State University, University Park, Pennsylvania 16802, USA.
J Am Chem Soc. 2008 Nov 12;130(45):14964-5. doi: 10.1021/ja807020d. Epub 2008 Oct 18.
The sponge metabolite dibromoagelaspongin was synthesized in 16 steps from imidazole. The route features two successive oxidative cyclizations with complete control of regiochemistry to deliver the unusual triaminomethane core of the target. These oxidative cyclizations likely resulted from Pummerer-like processes on the imidazole-2-sulfoxide (sulfide) precursors.
海绵代谢产物二溴琼脂海绵素由咪唑经16步合成。该路线的特点是两次连续的氧化环化反应，对区域化学具有完全控制，从而得到目标物不同寻常的三氨基甲烷核心结构。这些氧化环化反应可能源于咪唑-2-亚砜（硫化物）前体上类似普默勒尔反应的过程。
