Total Synthesis of Aquayamycin

Kusumi Shunichi; Nakayama Harunobu; Kobayashi Takumi; Kuriki Hajime; Matsumoto Yuka; Takahashi Daisuke; Toshima Kazunobu

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Total Synthesis of Aquayamycin

机译：阿卡霉素的全合成

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An efficient and practical total synthesis of aquayamycin has been accomplished. The highly oxidized and stereochemically complex tetracyclic ring system was constructed using three key reactions: 1) highly diastereo-selective 1,2-addition of C-glycosyl naphthyllithium to a cyclic ketone, 2) indium-mediated site-selective allylation-rearrangement sequence of naphthoquinone, and 3) diastereoselective intramolecular pinacol coupling. This synthetic strategy offers a novel and efficient pathway to prepare aquayamycin-type angucycline antibiotics.

机译：已经完成了高效和实用的水霉素全合成。高氧化和立体化学复杂的四环体系是通过三个关键反应构建的：1）C-糖基萘基锂对环酮的高非对映选择性1,2-加成，2）铟介导的位点选择性烯丙基化重排序列萘醌，和3）非对映选择性分子内频哪醇偶联。这种合成策略为制备水霉素型安古环素抗生素提供了新颖有效的途径。

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《Chemistry: A European journal》 |2016年第52期|共4页
作者
Kusumi Shunichi; Nakayama Harunobu; Kobayashi Takumi; Kuriki Hajime; Matsumoto Yuka; Takahashi Daisuke; Toshima Kazunobu;
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正文语种 eng
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angucycline antibiotics; antitumor antibiotics; aquayamycin; natural products; total synthesis;

机译：安古环素抗生素;抗肿瘤抗生素;水霉素;天然产物;全合成;

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1. Total Synthesis of Aquayamycin [J] . Kusumi Shunichi, Nakayama Harunobu, Kobayashi Takumi, Chemistry: A European journal . 2016,第52期

机译：阿卡霉素的全合成
2. Lipase-catalyzed asymmetrization of diacetate of meso-2-(2-propynyl)cyclohexane-1,2,3-triol toward the total synthesis of aquayamycin [J] . Matsumoto T., Yamaguchi H., Nakamura T., Synlett . 2001,第10期

机译：脂肪酶催化内消旋-2-（2-丙炔基）环己烷-1,2,3-三醇的双乙酸酯对水霉素的全合成
3. Total synthesis of augucyclines. Part 16:~1 8-Deoxy-urdamycinone F, a nonaromatic angucycline antibiotic of the aquayamycin type [J] . Karsten Krohn, Peter Frese Tetrahedron letters: The International Journal for the Rapid Publication of Preliminary Communications in Organic Chemistry . 2001,第4期

机译：全合成奥古环素。第16部分：〜1 8-脱氧尿嘧啶F，一种水霉素类型的非芳族安古环素抗生素
4. Totally self-checking FSM design based on multilevel synthesis methods and FPGA implementation [C] . A. Matrosova, K. Nikitin, O. Goloubeva IEEE International On-Line Testing Workshop . 2001

机译：基于多级合成方法和FPGA实现的全面自检FSM设计
5. Part I: The first regio- and atropdiastereoselective total synthesis of the dimeric indole alkaloid (+)-dispegatrine, as well as the first total synthesis of the sarpagine alkaloids (+)-spegatrine, lochvinerine, (+)-lochneram and an improved total synthesis of (+)-10-methoxyvellosimine, (+)-lochnerine and (+)-sarpagine. Part II: Studies directed toward the total synthesis of the carbon-19 methyl substituted sarpagine-macroline alkaloids (+)-macro-salhine chloride as well as macrocarpine A, B and C. [D] . Edwankar, Chitra R. 2011

机译：第一部分：二聚吲哚生物碱（+）-dispegatrine的第一个区域和对映异构选择性全合成，以及sarpagine生物碱（+）-spegatrine，lochvinerine，（+）-lochneram的第一个全合成（+）-10-甲氧基玻璃素胺，（+）-氯精胺和（+）-sarpagine的合成。第二部分：研究碳19甲基取代的沙雷帕金-大麦碱生物碱（+）-大-沙丁鱼碱氯化物以及大芸香碱A，B和C的总合成。
6. Natural Product Synthesis Special Feature: Prospects for total synthesis: A vision for a totally synthetic vaccine targeting epithelial tumors [O] . Stacy J. Keding, Samuel J. Danishefsky 2004

机译：天然产物合成特殊功能：全面合成的前景：针对上皮肿瘤的完全合成疫苗的愿景
7. Convergency and Divergency as Strategic Elements in Total Synthesis: The Total Synthesis of (−)-Drupacine and the Formal Total Synthesis of (±)-Cephalotaxine, (−)-Cephalotaxine, and (+)-Cephalotaxine [O] . Liu Qi, Ferreira Eric M., Stoltz Brian M. 2007

机译：收敛性和发散性是总合成中的战略要素：（-）-杜拉帕汀的总合成和（±）-头孢他辛，（-）-头孢他辛和（+）-头孢他定的形式的总合成

Total Synthesis of Aquayamycin

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