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A solution to the stereochemical problems posed by amaryllidaceae constituents using a highly syn-selective arylcuprate conjugate addition to γ-amino and γ-carbamato-α,β-enoates.一种通过高顺式选择性芳基铜酸盐对γ-氨基和γ-氨基甲酰基-α,β-烯酸酯进行共轭加成来解决石蒜科成分所带来的立体化学问题的方法。
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2
Selectivity guidelines and a reductive elimination-based model for predicting the stereochemical course of conjugate addition reactions of organocuprates to gamma-alkoxy-alpha,beta-enoates.用于预测有机铜酸盐与γ-烷氧基-α,β-烯酸酯共轭加成反应立体化学过程的选择性指导原则及基于还原消除的模型。
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1
Synthesis and biological evaluation of aromatic analogues of conduritol F, L-chiro-inositol, and dihydroconduritol F structurally related to the amaryllidaceae anticancer constituents.与石蒜科抗癌成分结构相关的康杜立醇F、L-手性肌醇和二氢康杜立醇F的芳香类似物的合成及生物学评价。
J Org Chem. 2006 Jul 21;71(15):5694-707. doi: 10.1021/jo0607562.
2
Selectivity guidelines and a reductive elimination-based model for predicting the stereochemical course of conjugate addition reactions of organocuprates to gamma-alkoxy-alpha,beta-enoates.用于预测有机铜酸盐与γ-烷氧基-α,β-烯酸酯共轭加成反应立体化学过程的选择性指导原则及基于还原消除的模型。
J Org Chem. 2006 Mar 31;71(7):2630-40. doi: 10.1021/jo052383v.
3
Cyclotrimerization strategy toward analogues of amaryllidaceae constituents. synthesis of deoxygenated pancratistatin core.针对石蒜科成分类似物的环三聚策略。脱氧 pancratistatin 核心的合成。
Org Lett. 2005 Dec 8;7(25):5669-72. doi: 10.1021/ol052372o.
4
Induction of apoptotic cell death specifically in rat and human cancer cells by pancratistatin.棒丝黄素特异性诱导大鼠和人类癌细胞发生凋亡性细胞死亡。
Artif Cells Blood Substit Immobil Biotechnol. 2005;33(3):279-95. doi: 10.1081/bio-200066621.
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Synthesis of 4-substituted-3-aminopiperidin-2-ones: application to the synthesis of a conformationally constrained tetrapeptide N-acetyl-Ser-Asp-Lys-Pro.
J Org Chem. 2005 Jul 22;70(15):5946-53. doi: 10.1021/jo050736k.
6
Pancratistatin: a natural anti-cancer compound that targets mitochondria specifically in cancer cells to induce apoptosis.泛癌抑素：一种天然抗癌化合物，可特异性作用于癌细胞中的线粒体以诱导细胞凋亡。
Apoptosis. 2005 May;10(3):619-30. doi: 10.1007/s10495-005-1896-x.
7
Reactions of indole derivatives with oxiranes and aziridines on silica. Synthesis of beta-carbolin-1-one mimic of pancratistatin.吲哚衍生物与二氧化硅上的环氧乙烷和氮丙啶的反应。泛喹酮β-咔啉-1-酮类似物的合成。
J Org Chem. 2005 Apr 29;70(9):3490-9. doi: 10.1021/jo040292c.
8
Pancratistatin causes early activation of caspase-3 and the flipping of phosphatidyl serine followed by rapid apoptosis specifically in human lymphoma cells.泛癌抑素可导致半胱天冬酶-3的早期激活和磷脂酰丝氨酸的翻转，随后在人淋巴瘤细胞中引发快速凋亡。
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9
Effects of lycorine on HL-60 cells via arresting cell cycle and inducing apoptosis.石蒜碱通过阻滞细胞周期和诱导凋亡对HL-60细胞产生的影响。
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10
A beta-carboline-1-one mimic of the anticancer Amaryllidaceae constituent pancratistatin: synthesis and biological evaluation.一种抗癌石蒜科成分潘克拉他汀的β-咔啉-1-酮类似物：合成与生物学评价。
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一种通过高顺式选择性芳基铜酸盐对γ-氨基和γ-氨基甲酰基-α,β-烯酸酯进行共轭加成来解决石蒜科成分所带来的立体化学问题的方法。

A solution to the stereochemical problems posed by amaryllidaceae constituents using a highly syn-selective arylcuprate conjugate addition to γ-amino and γ-carbamato-α,β-enoates.

作者信息

Rastogi Shiva K, Kornienko Alexander

机构信息

Department of Chemistry, New Mexico Institute of Mining and Technology, Socorro, NM 87801, USA.

出版信息

Tetrahedron Asymmetry. 2006 Nov 27;17(22):3170-3176. doi: 10.1016/j.tetasy.2006.11.029.

DOI:10.1016/j.tetasy.2006.11.029
PMID:22791936
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC3393039/
Abstract

Various substituted arylcuprates undergo stereocontrolled additions to L-serine-derived γamino- and γ-carbamato-α,β-enoates with high syn-selectivities. The stereochemical outcome of these reactions is fully consistent with the reductive elimination-based model proposed previously. This method is well suited for the preparation of a broad range of biologically active amaryllidaceae constituents and their aromatic analogues.

摘要

各种取代芳基铜酸盐能以高顺式选择性对L-丝氨酸衍生的γ-氨基和γ-氨基甲酰基-α,β-烯酸酯进行立体控制加成反应。这些反应的立体化学结果与先前提出的基于还原消除的模型完全一致。该方法非常适合制备多种具有生物活性的石蒜科成分及其芳香类似物。