Intramolecular Diels–Alder Reactions of Oxazoles, Imidazoles, and Thiazoles
Intramolecular Diels–Alder Reactions of Oxazoles, Imidazoles, and Thiazoles
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DOI：
10.1055/s-0040-1705991
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发表时间：
2020-12
期刊：
影响因子：
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通讯作者：
P. Wipf;T. T. Nguyen-T.
中科院分区：
文献类型：
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作者：
P. Wipf;T. T. Nguyen-T.
摘要 唑类杂环，即恶唑（IMDAO）、咪唑（IMDAI）和噻唑（IMDAT）的分子内Diels-Alder环加成反应的发展，对杂环中间体和天然产物的高效制备产生了重大影响。特别是，高效且通用的 IMDAO 反应已被用作多种合成方案中的关键步骤，以提供生物碱和萜类目标分子。对 IMDAI 和 IMDAT 环加成进行了更有限的研究。本综述还强调了一些缺点，例如 IMDA 前体的制备有时具有挑战性。提供了关于如何进一步扩展 IMDAI 和 IMDAT 转换以进行靶向合成的观点。 1 简介 2 恶唑 2.1 IMDAO 呋喃倍半萜和呋喃类固醇的合成方法 2.1.1 高含氧倍半萜的合成 2.1.2 (±)-格尼迪酮和 (±)-异格尼迪酮的合成 2.1.3 (±)-百部酰胺的合成 2.1.4 (±)-稗内酯A 2.1.5 (+)-和(–)-去甲红碱的合成 2.1.6 吴茱萸酮的合成 2.1.7 (±)-Ligularone 和 (±)-Petasalbine 的合成 2.1.8 Imerubrine、Isoimerubrine 和 Grandirubrine 的合成 2.1.9 呋喃类固醇的合成 2.1.10 取代的二氢吲哚和四氢喹啉 2.2 IMDAO 吡啶方法：Kondrat’eva 反应 2.2.1 Suaveoline 和 Norsuaveoline 的合成 2.2.2 Eupolauramine 的合成 2.2.3 (–)-Plectrodorine 和 (+)-Oxerine 的合成 2.2.4 Amphimedine 的合成 2.2.5综合方法 2.2.6 马林喹啉 A 的合成 2.2.6.1 马林喹啉 A 的 IMDAO 方法 2.2.6.2 烯基 IMDAO 环加成的范围 2.3 IMDAO 反应中的路易斯酸催化 2.3.1 铕催化剂对 IMDAO 反应的影响 2.3.2 铜催化剂的影响关于 IMDAO 反应 3 咪唑类 4 噻唑类 4.1 薄荷烷和 Eremophilane 的合成 4.2 对硫代羰基叶立德分子内环加成的进一步评论 5 结论与展望
Abstract The development of the intramolecular Diels–Alder cycloaddition of azole heterocycles, i.e. oxazoles (IMDAO), imidazoles (IMDAI), and thiazoles (IMDAT), has had a significant impact on the efficient preparation of heterocyclic intermediates and natural products. In particular, highly efficient and versatile IMDAO reactions have been utilized as a key step in several synthetic schemes to provide alkaloids and terpenoid target molecules. More limited studies have been performed on IMDAI and IMDAT cycloadditions. Some drawbacks, such as the occasionally challenging preparation of IMDA precursors, are also highlighted in this review. Perspectives are provided on how IMDAI and IMDAT transformations can be further expanded for target-directed syntheses. 1 Introduction 2 Oxazoles 2.1 IMDAO Approaches to Furanosesquiterpenes and Furanosteroids 2.1.1 Syntheses of Highly Oxygenated Sesquiterpenes 2.1.2 Syntheses of (±)-Gnididione and (±)-Isognididione 2.1.3 Synthesis of (±)-Stemoamide 2.1.4 Synthesis of (±)-Paniculide A 2.1.5 Syntheses of (+)- and (–)-Norsecurinine 2.1.6 Synthesis of Evodone 2.1.7 Syntheses of (±)-Ligularone and (±)-Petasalbine 2.1.8 Syntheses of Imerubrine, Isoimerubrine, and Grandirubrine 2.1.9 Syntheses of Furanosteroids 2.1.10 Syntheses of Substituted Indolines and Tetrahydroquinolines 2.2 IMDAO Approaches to Pyridines: the Kondrat’eva Reaction 2.2.1 Syntheses of Suaveoline and Norsuaveoline 2.2.2 Synthesis of Eupolauramine 2.2.3 Syntheses of (–)-Plectrodorine and (+)-Oxerine 2.2.4 Synthesis of Amphimedine 2.2.5 Synthetic Approach to the Western Segment of Haplophytine 2.2.6 Synthesis of Marinoquinoline A 2.2.6.1 IMDAO Approach to Marinoquinoline A 2.2.6.2 Scope of Allenyl IMDAO Cycloaddition 2.3 Lewis Acid Catalysis in IMDAO Reactions 2.3.1 Effects of Europium Catalysts on IMDAO Reactions 2.3.2 Effects of Copper Catalysts on IMDAO Reactions 3 Imidazoles 4 Thiazoles 4.1 Syntheses of Menthane and Eremophilane 4.2 Further Comments on the Intramolecular Cycloadditions of Thiocarbonyl Ylides 5 Conclusions and Outlook