Progress in the Synthesis of 3-Substituted Phthaides

doi:10.6023/cjoc202104063

Abstract

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

Cite this article

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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Fig. & Tab. 15

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

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

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

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

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

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

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

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

Scheme 7. Proposed mechanism for the Eq. 14

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

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

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

Scheme 11. Synthesis of Isoochracinic acid

Scheme 12. Synthesis of Isopestacin

Scheme 13. Synthesis of Bicuculline

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