Iterative deoxypropionate synthesis based on a copper-mediated directed allylic substitution: Formal total synthesis of borrelidin (C3-C11 fragment)

Herber C; Breit B

首页> 外文期刊>Chemistry: A European journal >Iterative deoxypropionate synthesis based on a copper-mediated directed allylic substitution: Formal total synthesis of borrelidin (C3-C11 fragment)

【24h】

Iterative deoxypropionate synthesis based on a copper-mediated directed allylic substitution: Formal total synthesis of borrelidin (C3-C11 fragment)

机译：基于铜介导的定向烯丙基取代的迭代脱氧丙酸酯合成：硼瑞林（C3-C11片段）的正式全合成

获取原文

获取原文并翻译 | 示例

掌桥外文数据库（机构版） >>

开具论文收录证明 >>

文献代查 >>

页面导航

摘要
著录项
相似文献
相关主题

摘要

A new iterative strategy for the flexible preparation of any oligodeoxypropionate stereoisomer is presented which relies on an o-DPPB-directed copper mediated allylic substitution employing enantiomerically pure Grignard reagents; the reaction is working with perfect control over all aspects of the reaction selectivity. This key C-C bond-forming step features reversed polarity compared with established enolate alkylation methodology. It thus avoids existing problems of enolate alkylation strategies such as enolate reactivity as well as costs and problems associated with the chiral auxiliary. Practicability of this new method is demonstrated through application in natural product syntheses. Thus, an efficient synthesis of the northern part of the angiogenesis inhibitor borrelidin (28), the deoxypropionate building block 27, could be devised, representing a formal total synthesis.

机译：提出了一种灵活制备任何低聚脱氧丙酸酯立体异构体的新的迭代策略，该策略依赖于对映体纯的格氏试剂的邻-DPPB-定向的铜介导的烯丙基取代。该反应在反应选择性的所有方面都得到了完美的控制。与已建立的烯醇烷基化方法相比，这一关键的C-C键形成步骤具有相反的极性。因此，它避免了烯醇盐烷基化策略的现有问题，例如烯醇盐反应性以及与手性助剂相关的成本和问题。通过在天然产物合成中的应用证明了这种新方法的实用性。因此，可以设计血管生成抑制剂硼瑞林（28）的北部，脱氧丙酸酯结构单元27的有效合成，代表正式的总合成。

著录项

来源
《Chemistry: A European journal》 |2006年第25期|共8页
作者
Herber C; Breit B;
展开▼
作者单位

展开▼
收录信息
原文格式 PDF
正文语种 eng
中图分类化学;
关键词
allylation; asymmetric synthesis; diastereoselectivity; Grignard reagents; polyketides; CATALYZED ASYMMETRIC CARBOALUMINATION; ENANTIOSELECTIVE TOTAL-SYNTHESIS; PSEUDOMONAS-FLUORESCENS LIPASE; 2-METHYL-1; 3-PROPANEDIOL DERIVATIVES; STEREOSELECTIVE-SYNTHESIS; CHEMOENZYMATIC APPROACH; CONJUGATE ADDITION; EFFICIENT; (-)-BORRELIDIN; IONOMYCIN;

机译：烯丙基化;不对称合成;非对映选择性;格氏试剂;聚酮化合物;催化的不对称碳铝化;对映选择性合成;磷酸单氟酯酶;2-甲基-1;3-丙醛衍生物;对映异构体;对映异构体;对映体;对映体;对映体;对映体-）-BORRELIDIN;离子霉素;

相似文献

外文文献
专利

1. Iterative deoxypropionate synthesis based on a copper-mediated directed allylic substitution: Formal total synthesis of borrelidin (C3-C11 fragment) [J] . Herber C, Breit B Chemistry: A European journal . 2006,第25期

机译：基于铜介导的定向烯丙基取代的迭代脱氧丙酸酯合成：硼瑞林（C3-C11片段）的正式全合成
2. Formal total synthesis of borrelidin: synthesis of C1-C11 fragment via desymmetrization strategy [J] . J. S. Yadav, Padmavani Bezawada, Venugopal Chenna Tetrahedron letters: The International Journal for the Rapid Publication of Preliminary Communications in Organic Chemistry . 2009,第27期

机译：硼瑞林的正式全合成：通过去对称化策略合成C1-C11片段
3. O-DPPB-Directed copper-mediated allylic substitution: Part 3. Stereospecific and stereodivergent construction of tertiary and quaternary carbon centers through switchable directedondirected allylic substitution [J] . Breit B, Demel P, Grauer D, Chemistry, an Asian journal . 2006,第4期

机译：O-DPPB定向的铜介导的烯丙基取代：第3部分。通过可转换的有向/无定向的烯丙基取代，第三和第四碳中心的立体特异性和立体发散性
4. From Allylic Substitution Catalyzed by Ruthenium Complexes to the Total Synthesis of (+)-iso-exo-Brevicomin [C] . Jean-Luc RENAUD, Asmae Bouziane, Francois CARREAUX European Symposium on Organic Chemistry . 2009

机译：由钌配合物催化的烯丙基替代取代，以（+） - ISO-EXO-Brevicomin的总合成
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. Oxidative allylic rearrangement of cycloalkenols: Formal total synthesis of enantiomerically pure trisporic acid B [O] . Silke Dubberke, Muhammad Abbas, Bernhard Westermann 2011

机译：环烯醇的氧化烯丙基重排：对映体纯的三孢酸B的正式全合成
7. Studies on the Total Synthesis of Amphidinolide O. A Stereoselective Synthesis of C3-C11 Fragment [O] . 2003

机译：amphidinolide的总合成的研究。C3-C11片段的立体选择性合成

Iterative deoxypropionate synthesis based on a copper-mediated directed allylic substitution: Formal total synthesis of borrelidin (C3-C11 fragment)

摘要

著录项

相似文献

相关主题

期刊订阅