3-取代苯酞的合成研究进展

doi:10.6023/cjoc202104063

摘要/Abstract

含3-取代苯酞结构的化合物广泛存在于植物和真菌中, 是传统中草药中的活性成分, 在现代医药中受到广泛关注. 本综述列举了部分具有生物活性的苯酞类化合物, 综述了3-取代苯酞类化合物的合成研究进展, 特别是近年来报道的对映体选择性合成方法, 以期对设计、发现具有广泛适用性和高立体选择性地合成苯酞骨架或类似化合物的方法产生启示作用. 这些方法包括: (a)通过形成C—C键的反应构建内酯, 例如2-酰基苯甲酸酯等的醇醛缩合/内酯化级联反应; (b)通过形成C—O键的反应构建内酯, 例如2-酰基苯甲酸酯的还原内酯化或3-烯基苯酞的还原, 分子内氧化/内酯化, 或分子内氧化还原/内酯化. 这些方法对于高立体选择性合成苯酞类化合物和药物研究具有重要意义.

关键词: 苯酞, 异苯并呋喃-1(3H)-酮, 合成, 对映选择性, 天然产物

3-Substituted phthalides are widely distributed in plants and fungi. They are active ingredients in traditional Chinese herbal medicines, and have attracted much attention in modern medicinal chemistry. The synthetic methods of 3-substituted phthalides are reviewed, especially those in enantioselective manners. The main approach involves: (a) construction of lactones from C—C bond formation reactions, e.g. an aldol/lactonization cascade reaction of 2-acylbenzoates and alikes, (b) construction of lactones via C—O bond formation reactions, e.g. reductive lactonization of 2-acylbenzoates or reduction of 3-alkenyl phthalides, intramolecular oxidation/lactonization, or intramolecular redox/lactonization. These methods are of great significance for the high stereoselective synthesis of phthalides and drug research.

Key words: phthalide, isobenzofuran-1(3H)-one, synthesis, enantioselectivity, natural product

引用此文

李泉城, 姜岚, 白瑞, 韩永康, 李争宁. 3-取代苯酞的合成研究进展[J]. 有机化学, 2021, 41(9): 3390-3399.

Quancheng Li, Lan Jiang, Rui Bai, Yongkang Han, Zhengning Li. Progress in the Synthesis of 3-Substituted Phthaides[J]. Chinese Journal of Organic Chemistry, 2021, 41(9): 3390-3399.

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图/表 15

图1. 苯酞基本结构及部分具有生物活性的苯酞类化合物

Figure 1. Basic structures of phthalide and some biologically active phthalides

图式1. 苯胺催化aldol加成/内酯化反应的可能机理

Scheme 1. Possible mechanism for the aniline-catalyzed aldol/lactonization cascade reaction

图2. 金属催化合成苯酞所用的的催化剂和配体

Figure 2. Structures of the catalysts and ligands in metal-catalyzed syntheses of phthalides

图式2. 亲核取代反应合成手性3-单取代苯酞

Scheme 2. Synthesis of 3-monosubstituted phthalides via a nucleophilic substitution reaction

图式3. Pd催化的芳基化/内酯化反应合成手性3-单取代苯酞

Scheme 3. Synthesis of chiral 3-monosubstituted phthalides via a Pd-catalyzed arylation/lactonization reaction

图式4. Cu催化直接羧化合成3-单取代苯酞

Scheme 4. Synthesis of 3-monosubstituted phthalides via a [Cu]-catalyzed direct carboxylation

图式5. Ru催化形成苯环的炔烃三聚反应

Scheme 5. Ru-catalyzed formation of benzene framework via cyclotrimerization reaction of alkynes

图式6. 碘化氢引发合成3-单取代苯酞

Scheme 6. Hydroiodination-triggered synthesis of 3-mono- substituted phthalides

图式7. Eq. 14可能的机理

Scheme 7. Proposed mechanism for the Eq. 14

图式8. 氧化/环化反应合成3-单取代苯酞

Scheme 8. Synthesis of 3-monosubstituted phthalides via an oxidative/cyclization reaction

图式9. Cannizarro-Tishchenko反应合成3-单取代苯酞

Scheme 9. Synthesis of 3-monosubstituted phthalides via a Cannizarro-Tishchenko reaction

图式10. Ir催化加氢酰化催化循环

Scheme 10. Catalytic cycle of [Ir]-catalyzed hydroacylation

图式11. Isoochracinic acid的合成

Scheme 11. Synthesis of Isoochracinic acid

图式12. Isopestacin的合成

Scheme 12. Synthesis of Isopestacin

图式13. Bicuculline的合成

Scheme 13. Synthesis of Bicuculline

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