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采用SAMP/RAMP腙方法对(-)-吡咯菌素进行不对称全合成。

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

作者信息

Enders Dieter, Dhulut Sylvie, Steinbusch Daniel, Herrbach Audrey

机构信息

Institut für Organische Chemie, RWTH Aachen, Landoltweg 1, 52074 Aachen, Germany.

出版信息

Chemistry. 2007;13(14):3942-9. doi: 10.1002/chem.200601672.

Abstract

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 alpha-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.

摘要

本文描述了对具有免疫抑制、抗肿瘤和植物生长调节活性的聚酮化合物吡柔比星(1)进行的汇聚式不对称全合成。该合成通过使用向山-醇醛反应分别将C(8)-C(14)片段2和C(7)-C(2)片段15进行偶联来实现。每个片段的手性中心通过采用SAMP/RAMP腙(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)方法作为关键步骤来构建。二乙酮 的不对称α-烷基化反应使得能够引入片段2的C(10)手性中心,而片段15的C(4)和C(5)手性中心则通过不对称醇醛反应构建。最后,在催化量的四异丙醇钛存在下通过闭环复分解反应实现了α,β-不饱和δ-内酯的形成。

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