Total Synthesis of Aigialomycin D Using a Ramberg-Backlund/RCM Strategy
Total Synthesis of Aigialomycin D Using a Ramberg-Backlund/RCM Strategy
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DOI：
10.1021/jo802561s
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发表时间：
2009-03-20
影响因子：
3.6
通讯作者：
Harvey, Joanne E.
中科院分区：
文献类型：
--
作者：
Baird, Lynton J.;Timmer, Mattie S. M.;Harvey, Joanne E.
采用闭合环复分解（RCM）和Ramberg-Backlund反应合成了具有生物活性的间环酸内酯aigalomycin D(1)。这种合成策略使得C1‘-C2’烯烃在形成大环时，通过在C7‘-C8’烯烃上的合环复合反应，使C1‘-C2’烯烃被掩盖为砜，从而避免了环己烯的竞争性形成。随后的Ramberg-Backlund反应有效地生成C1'-C2' e -烯烃。这种RCM/Ramberg-Backlund联合反应策略在大环二烯的合成中具有广泛的应用前景。
The bioactive resorcylic acid lactone aigialomycin D (1) has been synthesized by a novel combination of ring-closing metathesis (RCM) and Ramberg-Backlund reactions. This synthetic strategy enables the C1'-C2' alkene to be masked as a sulfone during formation of the macrocycle by ring closing metathesis at the C7'-C8' olefin, thus avoiding competing formation of a cyclohexene. A subsequent Ramberg-Backlund reaction efficiently produces the C1'-C2' E-alkene. This combined RCM/Ramberg-Backlund reaction strategy should be widely applicable to the synthesis of macrocyclic dienes.