Stereocontrolled Cyclic Nitrone Cycloaddition Strategy for the Synthesis of Pyrrolizidine and Indolizidine Alkaloids

Alberto Brandi; Francesca Cardona; Stefano Cicchi; Franca M. Cordero; Andrea Goti

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Stereocontrolled Cyclic Nitrone Cycloaddition Strategy for the Synthesis of Pyrrolizidine and Indolizidine Alkaloids

机译：立体控制环硝基环加成反应合成吡咯烷和吲哚并立生物碱

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摘要

The synthesis of polyhydroxylated indolizidines and pyrrolizidines belonging to the class of iminosugars, endowed with a vast and assorted biological activity, can be achieved in a straightforward manner by a general strategy consisting of a highly stereoselective 1,3-dipolar cycloaddition of polyhydroxylated pyrroline-N-oxides followed by simple transformations of the isoxazolidine adducts. The strategy allows the complete control of the relative and absolute stereochemistry of the numerous stereogenic centers decorating these compounds.

机译：具有广泛而多样的生物学活性的亚氨基糖类多羟基吲哚并咪唑和吡咯并核苷的合成，可以通过直接策略由包括多羟基化吡咯啉-N的高度立体选择性1，3-偶极环加成的一般策略以简单的方式实现。 -氧化物，然后简单转化异恶唑烷加合物。该策略可以完全控制装饰这些化合物的众多立体中心的相对和绝对立体化学。

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来源
《Chemistry: A European journal》 |2009年第32期|共14页
作者
Alberto Brandi; Francesca Cardona; Stefano Cicchi; Franca M. Cordero; Andrea Goti;
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正文语种 eng
中图分类应用化学;
关键词
cycloaddition; glycosidase inhibitors; iminosugars; nitrones; pyrrolizidines;

机译：环加成;糖苷酶抑制剂;亚氨基糖;硝酮;吡咯烷;

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1. Stereocontrolled Cyclic Nitrone Cycloaddition Strategy for the Synthesis of Pyrrolizidine and Indolizidine Alkaloids [J] . Alberto Brandi, Francesca Cardona, Stefano Cicchi, Chemistry: A European journal . 2009,第32期

机译：立体控制环硝基环加成反应合成吡咯烷和吲哚并立生物碱
2. Synthesis of pyrrolizidine alkaloids via 1,3-dipolar cycloaddition involving cyclic nitrones and unsaturated lactones [J] . Stecko S, Jurczak M, Urbanczyk-Lipkowska Z, Carbohydrate research . 2008,第13期

机译：通过涉及环硝酮和不饱和内酯的1，3-偶极环加成反应合成吡咯烷嗪生物碱
3. NHC-mediated cross-coupling of sugar-derived cyclic nitrones with enals: general and efficient synthesis of polyhydroxylated pyrrolizidines and indolizidines [J] . Wen-Yuan Xu, Ren lwaki, Yue-Mei Jia, Organic & biomolecular chemistry . 2013,第28期

机译：NHC介导的糖衍生的环硝酮与enals的交叉偶联：多羟基吡咯烷并吲哚并立定的常规和有效合成
4. An RCM strategy for the enantiosynthesis of new polyhydroxylated quinolizidines, indolizidines and pyrrolizidines(Abstracts) [C] . Alessandro Sacchetti, Giordano Lesma, Alessia Colombo European Symposium on Organic Chemistry . 2007

机译：新型多羟基化喹硫吡啶，吲哚状物和吡咯醇（摘要）对映映的RCM策略（摘要）
5. Intramolecular cycloadditions of azides with olefins: Synthetic approaches to pyrrolizidine and indolizidine alkaloids. [D] . Williams, John Patrick. 1991

机译：叠氮化物与烯烃的分子内环加成：吡咯嗪和吲哚并立生物碱的合成方法。
6. Total Synthesis of Indolizidine Alkaloid (−)-209D: Overriding Substrate Bias in the Asymmetric Rhodium-Catalyzed 2+2+2 Cycloaddition [O] . Robert T. Yu, Ernest E. Lee, Guillaume Malik, -1

机译：吲哚并立定生物碱（-）-209D的全合成：在不对称铑催化的2 + 2 + 2环加成反应中的重要底物偏置
7. Synthesis of d-arabinose-derived polyhydroxylated pyrrolidine, indolizidine and pyrrolizidine alkaloids. Total synthesis of hyacinthacine A2 [O] . Delso, J. Ignacio, Tejero, Tomás, Goti, Andrea, 2010

机译：d-阿拉伯糖衍生的多羟基化吡咯烷，吲哚并立定和吡咯并立定生物碱的合成。葫芦素A2的全合成

Stereocontrolled Cyclic Nitrone Cycloaddition Strategy for the Synthesis of Pyrrolizidine and Indolizidine Alkaloids

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