Total synthesis of pipecolic acid and 1-C-alkyl 1,5- iminopentitol derivatives by way of stereoselective aldol reactions from (S)-isoserinal

Sebastian Baś; Rafat Kusy; Monika Pasternak-Suder; Cyril Nicolas; Jacek Mlynarski; Olivier R. Martin

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Total synthesis of pipecolic acid and 1-C-alkyl 1,5- iminopentitol derivatives by way of stereoselective aldol reactions from (S)-isoserinal

机译：通过（S）-异丝氨酸的立体选择性羟醛反应全合成哌啶酸和1-C-烷基1,5-亚氨基戊醇衍生物

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A short synthesis of iminosugars and pipecolic acid derivatives has been realized through aldol addition of a pyruvate, a range of ketones and (S)-isoserinal, followed by catalytic reductive intramolecular amination. The stereoselective aldol reaction was achieved successfully by using tertiary amines or di-zinc aldol catalysts, thus constituting two parallel routes to optically pure products with good yields and high diastereo-selectivities. These carbohydrate analogues may be the inhibitors of potent glycosidases and g lycosy Itransferases.

机译：亚氨基糖和胡椒酸衍生物的简短合成已通过醛醇添加丙酮酸酯，一系列酮和（S）-异丝氨酸的醛醇缩合，然后进行催化还原性分子内胺化来实现。通过使用叔胺或二锌羟醛催化剂成功地完成了立体选择性羟醛反应，从而构成了两条平行路线，以高收率和高非对映选择性获得了光学纯净的产物。这些碳水化合物类似物可能是有效的糖苷酶和糖基转移酶的抑制剂。

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《Organic & biomolecular chemistry》 |2018年第7期|1118-1125|共8页
作者
Sebastian Baś; Rafat Kusy; Monika Pasternak-Suder; Cyril Nicolas; Jacek Mlynarski; Olivier R. Martin;
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Faculty of Chemistry, Jagiellonian University, Gronostajowa 2, 30-387 Krakow, Poland;

Faculty of Chemistry, Jagiellonian University, Gronostajowa 2, 30-387 Krakow, Poland;

Faculty of Chemistry, Jagiellonian University, Gronostajowa 2, 30-387 Krakow, Poland;

Institut de Chimie Organique et Analytique, UMR CNRS 7311, Université d'Orléans, BP 6759, 45067 Orleans cedex 2, France;

Faculty of Chemistry, Jagiellonian University, Gronostajowa 2, 30-387 Krakow, Poland,Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, Poland;

Institut de Chimie Organique et Analytique, UMR CNRS 7311, Université d’Orléans, BP 6759, 45067 Orleans cedex 2, France;

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Total synthesis of pipecolic acid and 1-C-alkyl 1,5- iminopentitol derivatives by way of stereoselective aldol reactions from (S)-isoserinal

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