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Asymmetric total synthesis of (-)-pironetin employing the SAMP/RAMP hydrazone methodology

机译:使用SAMP / RAMP methodology方法进行(-)-吡咯烷酮的不对称全合成

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摘要

A convergent asymmetric total synthesis of pironetin (1), a polyketide with immunosuppressive, antitumor, and plant-growth regulating activities is described. The synthesis was realized by coupling between the C-8-C-14 2 and C-7-C-2 15 fragments, respectively, by using a Mukaiyama-aldol reaction. The stereogenic centers of each fragment were generated by employing the SAMP/RAMP hydrazone (SAMP (S)-1-amino-2-methoxymethylpyrrolidine, RAMP= (R)-1-amino-2-methoxymethylpyrrolidine) methodology as a key step. An asymmetric a-alkylation of diethyl ketone permitted the introduction of the C-10 stereogenic center of 2, whereas the stereocenters C-4 and C-5 of 15 were installed by an asymmetric aldol reaction. Finally, the formation of the alpha,beta-unsaturated delta-lactone was achieved by ring-closing metathesis in the presence of catalytic amounts of titanium tetraisopropoxide.
机译:描述了聚合的不对称全合成的吡咯丁酮(1),一种具有免疫抑制,抗肿瘤和植物生长调节活性的聚酮化合物。通过使用Mukaiyama-aldol反应分别通过在C-8-C-14 2和C-7-C-2 15片段之间偶联来实现合成。通过使用SAMP / RAMP((SAMP(S)-1-氨基-2-甲氧基甲基吡咯烷,RAMP =(R)-1-氨基-2-甲氧基甲基吡咯烷)作为关键步骤,生成每个片段的立体异构中心。二乙基酮的不对称a-烷基化允许引入2的C-10立体中心,而15的立体中心C-4和C-5通过不对称的醛醇缩合反应安装。最后,在催化量的四异丙氧基钛存在下,通过闭环复分解实现了α,β-不饱和δ-内酯的形成。

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